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174:, which employed a chiral boron Lewis acid-catalyst in combination with allyltrimethylsilane. Numerous catalytic enantioselective methods for carbonyl allylation followed, including work by Umani-Ronchi and Keck. While these methods had a significant impact, they do not circumvent the use of preformed allylmetal reagents. Catalytic variants of the
359:
Iridium-catalyzed transfer-hydrogenative carbonyl allylation method has been applied to the synthesis of polyketide natural products. Some examples are shown below. In every case, the target compound was prepared in significantly fewer steps than was previously achieved. For example, total syntheses
181:
Whereas the allylmetal reagents used in these first-generation technologies are often difficult to prepare and handle, the
Krische allylation exploits highly tractable allylic acetates. Additionally, the Krische allylation avoids the use of preformed allyl metal reagents or metallic reductants and
142:
reactants, hydrogen transfer from 2-propanol. Unlike other allylation methods, the
Krische allylation avoids the use of preformed allyl metal reagents and enables the direct conversion of primary alcohols to secondary homoallylic alcohols (precluding alcohol to aldehyde oxidation).
383:
in 17 LLS and 32 total steps. Through the use of the
Krische allylation, this synthesis was accomplished via a much shorter route than previous syntheses. The Krische allylation to his synthesis of callyspongiolide using the chiral
438:"Enantioselective Iridium-Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level via Transfer Hydrogenative Coupling of Allyl Acetate: Departure from Chirally Modified Allyl Metal Reagents in Carbonyl Addition"
167:. Subsequently, other chiral allylmetal reagents were developed by Kumada, Roush, Brown, Leighton, and others. These methods utilize preformed allyl metal reagents and generate stoichiometric quantities of metal byproducts.
338:
to the σ-allyliridium species VI triggers carbonyl addition by way of the six-centered transition structure VII to form the homoallylic alkoxide VIII. The homoallylic alkoxide VIII is stable with respect to
1369:"Total Synthesis of (+)-Roxaticin via C−C Bond Forming Transfer Hydrogenation: A Departure from Stoichiometric Chiral Reagents, Auxiliaries, and Premetalated Nucleophiles in Polyketide Construction"
1312:"Inversion of Enantioselectivity in Allene Gas versus Allyl Acetate Reductive Aldehyde Allylation Guided by Metal-Centered Stereogenicity: An Experimental and Computational Study"
717:"Diastereo- and enantioselective aldehyde addition reactions of 2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylic esters, a useful class of tartrate ester modified allylboronates"
678:"Asymmetric carbon-carbon bond formation via .beta.-allyldiisopinocampheylborane. Simple synthesis of secondary homoallylic alcohols with excellent enantiomeric purities"
388:
catalyst complex. ] In 2018, Harran also prepared callyspongiolide using the
Krische allylation as a convergent method for fragment union. Double crotylation was used by
343:
due to coordination of the double bond with the metal. Exchange with the primary alcohol reactant regenerates the iridium alkoxide I and releases the reaction product.
1032:"From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future"
138:, resulting in the formation of a secondary homoallylic alcohol. The mechanism of the Krische allylation involves primary alcohol dehydrogenation or, when using
283:
The figure below shows some of the different allyl donors that have been used in the
Krische allylation. These methods are summarized in the review literature.
223:
1092:"Catalytic Enantioselective Carbonyl Allylation and Propargylation via Alcohol-Mediated Hydrogen Transfer: Merging the Chemistry of Grignard and Sabatier"
512:"Enantioselective Alcohol C–H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis"
163:
natural products. In 1978, Hoffmann reported the first asymmetric carbonyl allylation using a chiral allylmetal reagent, an allylborane derived from
330:, which dissociates to form the iridium hydride III. Deprotonation of the iridium hydride III provides an anionic iridium(I) species IV, which upon
1149:"Protecting-Group-Free Diastereoselective CC Coupling of 1,3-Glycols and Allyl Acetate through Site-Selective Primary Alcohol Dehydrogenation"
303:-benzoate complex. This complex can be generated in situ or can be isolated via precipitation or conventional chromatography on silica gel.
175:
146:
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containing both primary and secondary alcohols undergo site-selective carbonyl allylation at the primary alcohol without the need for
1571:"Studies toward the Unique Pederin Family Member Psymberin: Full Structure Elucidation, Two Alternative Total Syntheses, and Analogs"
1861:
608:"Stereoselektive Synthese von Alkoholen, VII1) Optisch aktive Homoallylalkohole durch Addition chiraler Boronsäureester an Aldehyde"
105:
43:
36:
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were accomplished via double
Krische allylation of 1,3-propane diol. This method was also used in the synthesis of mandelalide A.
178:
reaction represent an alternative method for asymmetric carbonyl allylation, but stoichiometric metallic reductants are required.
86:
639:"Optically active allylsilanes. 2. High stereoselectivity in asymmetric reaction with aldehydes producing homoallylic alcohols"
58:
65:
1198:"Iridium-Catalyzed Allylation of Chiral β-Stereogenic Alcohols: Bypassing Discrete Formation of Epimerizable Aldehydes"
234:
or metallic reductants. A remarkable feature of these reactions is the ability to conduct carbonyl allylation from the
72:
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Costa, Anna Luisa; Piazza, Maria Giulia; Tagliavini, Emilio; Trombini, Claudio; Umani-Ronchi, Achille (July 1993).
32:
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The excellent functional group compatibility of the
Krische allylation combined with the tractability of the
409:
756:"Strained Silacycles in Organic Synthesis: A New Reagent for the Enantioselective Allylation of Aldehydes"
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1255:"Ethanol: Unlocking an Abundant Renewable C 2 ‐Feedstock for Catalytic Enantioselective C−C Coupling"
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Kinnaird, James W. A.; Ng, Pui Yee; Kubota, Katsumi; Wang, Xiaolun; Leighton, James L. (2002-07-01).
272:
pronucleophiles enables the use of allyl donors bearing highly complex nitrogen-rich substituents.
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235:
135:
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The mechanism of the
Krische allylation has been corroborated by DFT calculations. Entry into the
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331:
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1483:"Total Synthesis of Cryptocaryol A by Enantioselective Iridium-Catalyzed Alcohol C−H Allylation"
79:
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Kim, Seung Wook; Meyer, Cole C.; Mai, Binh Khanh; Liu, Peng; Krische, Michael J. (2019-10-04).
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Meyer, Cole C.; Stafford, Nicholas P.; Cheng, Melinda J.; Krische, Michael J. (2021-05-03).
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1675:"Unconventional Fragment Usage Enables a Concise Total Synthesis of (−)-Callyspongiolide"
1779:"Total Synthesis of Swinholide A: An Exposition in Hydrogen-Mediated C–C Bond Formation"
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1722:"Total Synthesis of 6-Deoxyerythronolide B via C–C Bond-Forming Transfer Hydrogenation"
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Schmitt, Daniel C.; Dechert-Schmitt, Anne-Marie R.; Krische, Michael J. (2012-12-21).
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Dechert-Schmitt, Anne-Marie R.; Schmitt, Daniel C.; Krische, Michael J. (2013-03-11).
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198:” carbon-carbon bond formations. In a series of papers published in the early 2000s,
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The active catalyst in the
Krische allylation is a cyclometallated π-allyliridium
1107:
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Enantioselective carbonyl allylations are frequently applied to the synthesis of
1674:
1627:
569:"Enantioselective Synthesis of Homoallyl Alcoholsvia Chiral Allylboronic Esters"
319:
171:
127:
21:
1673:
Manoni, Francesco; Rumo, Corentin; Li, Liubo; Harran, Patrick G. (2018-01-31).
842:"A practical and efficient method for enantioselective allylation of aldehydes"
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Han, Soo Bong; Hassan, Abbas; Kim, In Su; Krische, Michael J. (2010-11-10).
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In 1991, Yamamoto disclosed the first catalytic enantioselective method for
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to the allyl donor forms the π-allyliridium complex V. Association of the
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881:"Chiral (Acyloxy)borane Catalyzed Asymmetric Allylation of Aldehydes"
1481:
Perez, Felix; Waldeck, Andrew R.; Krische, Michael J. (2016-04-11).
1426:"Total Synthesis of Bryostatin 7 via C–C Bond-Forming Hydrogenation"
957:
Keck, Gary E.; Tarbet, Kenneth H.; Geraci, Leo S. (September 1993).
1628:"Total Synthesis and Stereochemical Assignment of Callyspongiolide"
1626:
Zhou, Jingjing; Gao, Bowen; Xu, Zhengshuang; Ye, Tao (2016-06-08).
510:
Feng, Jiajie; Kasun, Zachary A.; Krische, Michael J. (2016-05-04).
241:. Due to a kinetic preference for primary alcohol dehydrogenation,
803:"Asymmetric allylboration with B-allyl-2-(trimethylsilyl)borolane"
715:
Roush, William R.; Walts, Alan E.; Hoong, Lee K. (December 1985).
637:
Hayashi, Tamio; Konishi, Mitsuo; Kumada, Makoto (September 1982).
207:
1090:
Kim, Seung Wook; Zhang, Wandi; Krische, Michael J. (2017-09-19).
998:"The Development of the Asymmetric Nozaki–Hiyama–Kishi Reaction"
242:
1777:
Shin, Inji; Hong, Suckchang; Krische, Michael J. (2016-11-02).
379:
The
Krische bisallylation has been applied to the synthesis of
1030:
Santana, Catherine Gazolla; Krische, Michael J. (2021-05-07).
15:
436:
Kim, In Su; Ngai, Ming-Yu; Krische, Michael J. (2008-11-05).
1720:
Gao, Xin; Woo, Sang Kook; Krische, Michael J. (2013-03-20).
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could be converted to transient allylmetal nucleophiles via
1532:"Catalysis-Based Total Synthesis of Putative Mandelalide A"
318:
involves protonation of the cyclometallated π-allyliridium
1424:
Lu, Yu; Woo, Sang Kook; Krische, Michael J. (2011-09-07).
1569:
Feng, Yu; Jiang, Xin; De Brabander, Jef K. (2012-10-17).
920:"Catalytic asymmetric synthesis of homoallylic alcohols"
879:
Furuta, Kyoji; Mouri, Makoto; Yamamoto, Hisashi (1991).
249:. Additionally, by using alcohol reactants, the use of
996:
Hargaden, Gráinne C.; Guiry, Patrick J. (2007-11-05).
840:
Corey, E. J.; Yu, Chan Mo; Kim, Sung Soo (July 1989).
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Brown, Herbert C.; Jadhav, Prabhakar K. (April 1983).
606:
Hoffmann, Reinhard W.; Herold, Thomas (January 1981).
567:
Herold, Thomas; Hoffmann, Reinhard W. (October 1978).
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to prepare 6-deoxyerythronolide B and swinholide A.
375:
Krische allylation in the synthesis of bryostatin 7,
573:Angewandte Chemie International Edition in English
801:Short, Robert P.; Masamune, Satoru (March 1989).
1530:Willwacher, Jens; Fürstner, Alois (2014-04-14).
959:"Catalytic asymmetric allylation of aldehydes"
8:
253:α-stereogenic aldehydes, which are prone to
493:Strategies and Tactics in Organic Synthesis
186:, significantly reducing waste generation.
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42:Please improve this article by adding
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230:carbonyl allylation avoids preformed
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322:to generate the iridium alkoxide I.
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194:The Krische allylation involves “
126:iridium-catalyzed addition of an
202:and coworkers demonstrated that
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495:, Volume 10 Michael Harmata Ed.
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1096:Accounts of Chemical Research
44:secondary or tertiary sources
1108:10.1021/acs.accounts.7b00308
326:of alkoxide I generates the
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355:Applications in synthesis
1862:Organometallic chemistry
1328:10.1021/acscatal.9b03695
1048:10.1021/acscatal.1c01109
624:10.1002/cber.19811140139
341:beta-hydride elimination
410:Organostannane addition
232:organometallic reagents
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220:transfer hydrogenation
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226:. This strategy for
55:"Krische allylation"
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415:Carbonyl allylation
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310:Catalytic cycle 1-2
176:Nozaki-Hiyama-Kishi
172:carbonyl allylation
612:Chemische Berichte
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1857:Catalysis
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