213:
245:
268:
332:
22:
610:
Roth, Lepke (1972). "Synthese von Indol- und
Carbazol-Derivaten aus α-Hydroxyketonen und aromatischen Aminen" [Synthesis of indole and carbazole derivatives from α-hydroxyketones and aromatic amines].
435:
Davis, Franklin A.; Vishwakarma, Lal C.; Billmers, Joanne G.; Finn, John (1984). "Synthesis of α-hydroxycarbonyl compounds (acyloins): direct oxidation of enolates using 2-sulfonyloxaziridines".
308:
375:
463:
Davis, F. A.; Haque, M. S.; Ulatowski, T. G.; Towson, J. C. (1986). "Asymmetric oxidation of ester and amide enolates using new (camphorylsulfonyl)oxaziridines".
499:
212:
244:
594:
340:
554:
267:
236:
660:
586:
531:
204:
85:, distinguished by the position of the hydroxy group relative to the ketone; in this form, the hydroxy is on the
355:, a related molecule equivalent to an acyloin with both R groups as hydrogen (and thus an aldehyde not a ketone)
252:
665:
183:
161:
331:
322:
220:
187:
113:
106:
409:
636:
137:
70:
405:
670:
628:
590:
523:
301:
294:
290:
280:
30:
231:(camphorsulfonyl oxaziridine). Each isomer gives exclusive access to one of the two possible
620:
563:
515:
473:
445:
389:
42:
507:
251:
In the enolate oxidation of the cyclopentaenone below with either camphor enantiomer, the
82:
352:
262:
position is limited. The use of the standard oxaziridine did not result in an acyloin.
224:
179:
654:
465:
437:
50:
640:
385:
495:
58:
307:
Some acyloins rearrange with positions swapped under the influence of base in the
380:
191:
117:
232:
150:
74:
624:
567:
384:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
393:
527:
632:
157:
153:
146:
123:
477:
449:
129:
Better alternative is oxidation of corresponding silyl enol ethers with
228:
175:
21:
519:
86:
549:
550:"Ueber die Einwirkung von primären aromatischen Aminen auf Benzoïn"
203:
When sulfonyloxaziridines oxidize enol(ate)s, the latter reacts by
318:
142:
130:
20:
284:
171:
101:
Classic organic reactions exist for the synthesis of acyloins.
552:[On the effect of primary aromatic amines on benzoin].
69:
is derived from the fact that they are formally derived from
190:. In a more elaborate version, enolates can be oxidized by
207:
at the electron deficient oxygen of the oxaziridine ring.
116:
is condensation reaction between aldehydes catalyzed by a
258:
is obtained because access for the hydroxyl group in the
182:
oxidizes a carbonyl to an α‑hydroxylamine, with a
500:"An Electrochemical Approach to the Guanacastepenes"
126:
is possible with molecular oxygen but not selective
167:A family of stereoselective syntheses oxidizes
583:Amines: Synthesis, Properties and Applications
300:α-hydroxy ketones give positive Tollens' and
8:
371:
369:
309:Lobry–de Bruyn–van Ekenstein transformation
81:). They are one of the two main classes of
16:Organic compounds of the form –C(=O)C(OH)–
489:
487:
494:Hughes, Chambers C.; Miller, Aubry K.;
365:
317:where an acyloin reacts with a primary
178:equivalents. In the simplest version,
410:"Catalytic Enantioselective Synthesis"
235:. This modification is applied in the
7:
313:A similar reaction is the so-called
548:von Meyer, E.; Voigt, Karl (1886).
89:, explaining the secondary name of
25:The structure of a typical acyloin.
381:Compendium of Chemical Terminology
219:This reaction type is extended to
14:
199:Oxidation with Sulfonyloxaridines
109:is a reductive coupling of esters
330:
266:
243:
211:
416:. Organic Chemistry Highlights
1:
581:Lawrence, Stephen A. (2004).
237:Holton taxol total synthesis
687:
587:Cambridge University Press
339:Indole synthesis, compare
227:oxaziridines derived from
205:nucleophilic displacement
625:10.1002/ardp.19723050302
568:10.1002/prac.18860340101
414:Organic Chemistry Portal
406:Taber, Douglass F.
394:10.1351/goldbook.A00126
162:hexamethylphosphoramide
184:proline organocatalyst
26:
24:
613:Archiv der Pharmazie
537:on 4 September 2006.
323:phosphorus pentoxide
221:asymmetric synthesis
192:sulfonyloxaziridines
114:benzoin condensation
107:acyloin condensation
45:of the general form
478:10.1021/jo00362a053
450:10.1021/jo00191a048
408:(26 January 2004).
325:to an α-keto amine:
138:Rubottom oxidation
71:reductive coupling
47:R−C(=O)−CR'(OH)−R"
27:
661:Functional groups
596:978-0-521-78284-5
520:10.1021/ol047387l
514:(16): 3425–3428.
444:(17): 3241–3243.
293:of acyloins give
283:of acyloins give
149:is a system with
43:organic compounds
39:α-hydroxy ketones
31:organic chemistry
678:
645:
644:
607:
601:
600:
578:
572:
571:
545:
539:
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536:
530:. Archived from
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453:
432:
426:
425:
423:
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402:
396:
373:
334:
270:
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188:enantioselection
91:α-hydroxy ketone
80:
64:
57:) adjacent to a
56:
49:, composed of a
48:
686:
685:
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651:
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555:J. Prakt. Chem.
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349:
341:Bischler–Möhlau
315:Voigt amination
277:
201:
99:
83:hydroxy ketones
78:
62:
54:
46:
41:are a class of
17:
12:
11:
5:
684:
682:
674:
673:
668:
666:Hydroxyketones
663:
653:
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647:
646:
619:(3): 159–171.
602:
595:
573:
540:
483:
455:
427:
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364:
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361:
358:
357:
356:
353:Glycolaldehyde
348:
345:
344:
343:
336:
335:
327:
326:
311:
305:
302:Fehling's test
298:
288:
276:
273:
272:
271:
249:
248:
223:by the use of
217:
216:
200:
197:
196:
195:
180:nitrosobenzene
165:
140:
127:
120:
110:
98:
95:
73:of carboxylic
15:
13:
10:
9:
6:
4:
3:
2:
683:
672:
669:
667:
664:
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659:
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615:(in German).
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584:
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569:
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558:(in German).
557:
556:
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497:
496:Trauner, Dirk
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468:
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466:J. Org. Chem.
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438:J. Org. Chem.
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145:oxidation of
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139:
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128:
125:
122:Oxidation of
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119:
115:
111:
108:
104:
103:
102:
96:
94:
92:
88:
84:
76:
72:
68:
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52:
51:hydroxy group
44:
40:
36:
32:
23:
19:
616:
612:
605:
582:
576:
559:
553:
543:
532:the original
511:
506:
472:(12): 2402.
469:
464:
458:
441:
436:
430:
418:. Retrieved
413:
400:
379:
314:
259:
253:
250:
218:
202:
168:
131:
100:
90:
87:alpha carbon
66:
65:). The name
59:ketone group
38:
34:
28:
18:
562:(1): 1–27.
233:enantiomers
118:nucleophile
75:acyl groups
655:Categories
508:Org. Lett.
360:References
151:molybdenum
291:Oxidation
281:Reduction
275:Reactions
147:carbonyls
124:carbonyls
97:Synthesis
671:Acyloins
641:84990819
528:16048308
498:(2005).
386:acyloins
347:See also
158:pyridine
154:peroxide
79:R−C(=O)−
35:acyloins
633:5048240
229:camphor
176:nitroso
169:in situ
136:in the
67:acyloin
63:>C=O
639:
631:
593:
526:
420:7 June
295:diones
256:isomer
225:chiral
637:S2CID
535:(PDF)
503:(PDF)
376:IUPAC
319:amine
285:diols
254:trans
174:with
172:enols
143:MoOPH
629:PMID
591:ISBN
524:PMID
422:2024
321:and
186:for
160:and
134:CPBA
112:The
105:The
621:doi
617:305
564:doi
516:doi
474:doi
446:doi
390:doi
388:".
260:cis
55:−OH
37:or
29:In
657::
635:.
627:.
589:.
585:.
560:34
522:.
505:.
486:^
470:51
442:49
412:.
378:,
368:^
239:.
156:,
93:.
33:,
643:.
623::
599:.
570:.
566::
518::
512:7
480:.
476::
452:.
448::
424:.
392::
304:.
297:.
287:.
194:.
164:.
132:m
77:(
61:(
53:(
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
