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of the formula PRR′R″, where R, R′, R″ = H, alkyl, aryl, etc. They are a subset of chiral phosphines, a broader class of compounds where the stereogenic center can reside at sites other than phosphorus. P-chirality exploits the high barrier for inversion of phosphines, which ensures that
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Mislow, Kurt; Baechler, Raymond D. (1971). "Effect of ligand electronegativity on the inversion barrier of phosphines".
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readily. The inversion barrier is relatively insensitive to substituents for triorganophosphines. By contrast, most
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100:-Chiral phosphines have been investigated for two main applications, as
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and related reactions. DIPAMP is prepared by coupling the
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78:. These chelating ligands support catalysts used in
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133:"Chiral Phosphines in Nucleophilic Organocatalysis"
364:Ultraviolet–visible spectroscopy of stereoisomers
92:-Chiral phosphines are of particular interest in
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131:Xiao, Y.; Sun, Z.; Guo, H.; Kwon, O. (2014).
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182:Journal of the American Chemical Society
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137:Beilstein Journal of Organic Chemistry
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86:-chiral methylphenylanisylphosphine.
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359:NMR spectroscopy of stereoisomers
47:of the type NRR′R″ undergo rapid
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397:Diastereomeric recrystallization
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39:enantiomers of PRR'R" do not
529:. You can help Knowledge by
472:. You can help Knowledge by
392:Chiral column chromatography
59:Most chiral phosphines are
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508:
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354:Chiral derivatizing agents
235:enantioselective synthesis
36:organophosphorus compounds
24:-chiral "Kwon phosphines".
280:Supramolecular chirality
80:asymmetric hydrogenation
606:Chemical reaction stubs
108:and as nucleophiles in
70:. Famous examples are
611:Chemical process stubs
581:Coordination chemistry
25:
601:Stereochemistry stubs
418:Chiral pool synthesis
332:Diastereomeric excess
106:homogeneous catalysts
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428:Asymmetric catalysis
413:Asymmetric induction
94:asymmetric catalysis
326:Enantiomeric excess
194:10.1021/ja00732a036
149:10.3762/bjoc.10.218
49:pyramidal inversion
423:Chiral auxiliaries
387:Kinetic resolution
285:Inherent chirality
270:-symmetric ligands
32:-Chiral phosphines
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382:Recrystallization
374:Chiral resolution
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349:Optical rotation
294:Chiral molecules
259:Planar chirality
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586:Stereochemistry
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433:Organocatalysis
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321:Racemic mixture
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275:Axial chirality
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242:Chirality types
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110:organocatalysis
104:for asymmetric
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55:Research themes
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316:Meso compound
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143:: 2089–2121.
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531:expanding it
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474:expanding it
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438:Biocatalysis
311:Diastereomer
301:Stereoisomer
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254:Stereocenter
233:Concepts in
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68:diphosphines
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596:Phosphanes
570:Categories
306:Enantiomer
116:References
65:-symmetric
576:Catalysis
523:catalysis
406:Reactions
249:Chirality
342:Analysis
167:25246969
41:racemize
591:Ligands
158:4168899
102:ligands
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72:DIPAMP
45:amines
521:This
464:This
76:BINAP
527:stub
470:stub
334:(de)
328:(ee)
163:PMID
74:and
34:are
20:Two
190:doi
153:PMC
145:doi
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98:P
90:P
84:P
63:2
61:C
30:P
22:P
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