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Literature DB >> 22309467

Histidine-catalyzed asymmetric aldol addition of enolizable aldehydes: insights into its mechanism.

Abstract

Extensive studies of asymmetric cross-aldol addition between enolizable aldehydes are described and provide a deeper insight into histidine-catalyzed aldol additions. In particular, aspects of enantio- as well as diastereoselectivity of these reactions are discussed. Rules and predictions of configurative outcome are explained by using different transition-state models. These discussions are confirmed by extensive computations.

Entities: Chemical

Mesh：

Substances：
Aldehydes
Histidine

Year: 2012 PMID： 22309467 DOI： 10.1021/jo202558f

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

4 in total

1. Generation of stereochemically defined tetrasubstituted enolborinates by 1,4-hydroboration of α,β-unsaturated morpholine carboxamides with (diisopinocampheyl)borane.

Authors: Christophe Allais; Andy S Tsai; Philippe Nuhant; William R Roush
Journal: Angew Chem Int Ed Engl Date: 2013-10-15 Impact factor: 15.336

Histidine-catalyzed asymmetric aldol addition of enolizable aldehydes: insights into its mechanism.

1. Generation of stereochemically defined tetrasubstituted enolborinates by 1,4-hydroboration of α,β-unsaturated morpholine carboxamides with (diisopinocampheyl)borane.

2. Wittig Rearrangements of Boron-Based Oxazolidinone Enolates.

3. Catalytic discrimination between formyl groups in regio- and stereoselective intramolecular cross-aldol reactions.

4. Alternative application of an affinity purification tag: hexahistidines in ester hydrolysis.