Imperial College London

ProfessorAlanArmstrong

Faculty of Natural SciencesDepartment of Chemistry

Professor of Organic Synthesis
 
 
 
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Contact

 

+44 (0)20 7594 5876a.armstrong

 
 
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Location

 

501EMolecular Sciences Research HubWhite City Campus

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Summary

 

Publications

Citation

BibTex format

@article{Bures:2012:10.1039/c2sc01082h,
author = {Bures, J and Armstrong, A and Blackmond, DG},
doi = {10.1039/c2sc01082h},
journal = {CHEMICAL SCIENCE},
pages = {(1273--1277)--(1273--1277)},
title = {Kinetic correlation between aldehyde/enamine stereoisomers in reactions between aldehydes with alpha-stereocenters and chiral pyrrolidine-based catalysts},
url = {http://dx.doi.org/10.1039/c2sc01082h},
volume = {3},
year = {2012}
}

RIS format (EndNote, RefMan)

TY  - JOUR
AB - The formation of enamines between aldehydes with alpha-stereocenters and pyrrolidine-based catalysts that lack an acidic proton is examined by kinetic and spectroscopic studies. The reaction exhibits “kinetic stereospecificity” in that each enantiomer of the aldehyde initially reacts to form a specific enamine stereoisomer, prior to thermodynamic equilibration of the E and Z enamines. For the case of prolinate catalysts, each of the stereoisomeric enamines is correlated with a specific stereoisomeric oxazolidinone. The reactions of E and Z enamines with electrophiles such as DEAD lead to products of opposite stereochemistry. The product enantioselectivity observed depends on the extent to which the E and Z enamines are pre-equilibrated prior to reaction with the electrophile. General implications for selectivity in organocatalytic reactions are discussed.
AU - Bures,J
AU - Armstrong,A
AU - Blackmond,DG
DO - 10.1039/c2sc01082h
EP - 1277
PY - 2012///
SN - 2041-6520
SP - 1273
TI - Kinetic correlation between aldehyde/enamine stereoisomers in reactions between aldehydes with alpha-stereocenters and chiral pyrrolidine-based catalysts
T2 - CHEMICAL SCIENCE
UR - http://dx.doi.org/10.1039/c2sc01082h
VL - 3
ER -