ATTAINMENT OF SYN-SELECTIVITY FOR BORON-MEDIATED ASYMMETRIC ALDOL REACTIONS OF CARBOXYLIC ESTERS

Authors
LIU JF ABIKO A PEI ZH BUSKE DC MASAMUNE S
Citation
Jf. Liu et al., ATTAINMENT OF SYN-SELECTIVITY FOR BORON-MEDIATED ASYMMETRIC ALDOL REACTIONS OF CARBOXYLIC ESTERS, Tetrahedron letters, 39(14), 1998, pp. 1873-1876
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
14
Year of publication
1998
Pages
1873 - 1876
Database
ISI
SICI code
0040-4039(1998)39:14<1873:AOSFBA>2.0.ZU;2-2
Abstract
A new chiral reagent for syn-selective aldol reactions has been develo ped based on the recent finding that the stereochemistry of the boron- mediated aldol reaction of a carboxylic ester is controlled by the bul kiness of the alcohol moiety of the ester, by the proper choice of rea gents, and by the enolization conditions. This readily available, inex pensive reagent has been utilized in studies directed towards the synt hesis of the macrolide tedanolide. (C) 1998 Elsevier Science Ltd. All rights reserved.