Enamine versus oxazolidinone: what controls stereoselectivity in proline-catalyzed asymmetric aldol reactions?

Sharma, Akhilesh K. ; Sunoj, Raghavan B. (2010) Enamine versus oxazolidinone: what controls stereoselectivity in proline-catalyzed asymmetric aldol reactions? Angewandte Chemie International Edition, 49 (36). pp. 6373-6377. ISSN 1433-7851

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/anie.20...

Related URL: http://dx.doi.org/10.1002/anie.201001588

Abstract

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.

Item Type:Article
Source:Copyright of this article belongs to John Wiley and Sons, Inc.
Keywords:Aldol Reaction; Density Functional Calculations; Diastereoselectivity; Organocatalysis; Reaction Mechanisms
ID Code:109784
Deposited On:02 Aug 2017 12:28
Last Modified:02 Aug 2017 12:28

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