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Double diastereoselection in aldol reactions mediated by dicyclohexylchloroborane between L-erythrulose derivatives and chiral aldehydes. The Felkin-Anh versus cornforth dichotomy

Authors :
Marco, J. Alberto
Carda, Miguel
Diaz-Oltra, Santiago
Murga, Juan
Falomir, Eva
Roeper, Harald
Source :
Journal of Organic Chemistry. Oct 31, 2003, Vol. 68 Issue 22, 8577-8582
Publication Year :
2003

Abstract

Matched and mismatched diastereoselections are observed in aldol reactions of the B, B-dicyclohexylboron enolate of a protected L-erythrulose derivative with a range of chiral aldehydes. Within the Felkin-Anh paradigm, the stereochemical outcome of reactions with alpha-methyl aldehydes can be explained efficiently.

Details

Language :
English
ISSN :
00223263
Volume :
68
Issue :
22
Database :
Gale General OneFile
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsgcl.119290280