We thank IIT Bombay computer center and CMSD Hyderabad for generous computing time. A.K.S. is grateful to CSIR New Delhi for a senior research fellowship.
Enamine versus Oxazolidinone: What Controls Stereoselectivity in Proline-Catalyzed Asymmetric Aldol Reactions?†
Article first published online: 21 JUL 2010
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 49, Issue 36, pages 6373–6377, August 23, 2010
How to Cite
Sharma, Akhilesh K. and Sunoj, Raghavan B. (2010), Enamine versus Oxazolidinone: What Controls Stereoselectivity in Proline-Catalyzed Asymmetric Aldol Reactions?. Angew. Chem. Int. Ed., 49: 6373–6377. doi: 10.1002/anie.201001588
- Issue published online: 19 AUG 2010
- Article first published online: 21 JUL 2010
- Manuscript Revised: 21 MAY 2010
- Manuscript Received: 17 MAR 2010
- aldol reaction;
- density functional calculations;
- reaction mechanisms
Take the right path: Comparison of the oxazolidinone and enamine pathways in enantioselective aldol reactions by using density functional and ab initio transition states reveals that the oxazolidinone route does not provide the correct stereochemical outcome (see picture), whereas the enamine pathway predicts the correct stereoselectivity.