FACILE APPROACH TOWARDS THE SYNTHESIS OF HOMOCHIRAL FUNCTIONALIZED ALCOHOLS FROM UTYLDIMETHYLSILYL]-2,3-O-CYCLOHEXYLIDENE-L-THREOSE OF (L)-(-TARTARIC ACID ORIGIN())

Authors
CHATTOPADHYAY A DHOTARE B
Citation
A. Chattopadhyay et B. Dhotare, FACILE APPROACH TOWARDS THE SYNTHESIS OF HOMOCHIRAL FUNCTIONALIZED ALCOHOLS FROM UTYLDIMETHYLSILYL]-2,3-O-CYCLOHEXYLIDENE-L-THREOSE OF (L)-(-TARTARIC ACID ORIGIN()), Tetrahedron : asymmetry, 9(15), 1998, pp. 2715-2723
Citations number
46
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
15
Year of publication
1998
Pages
2715 - 2723
Database
ISI
SICI code
0957-4166(1998)9:15<2715:FATTSO>2.0.ZU;2-J
Abstract
(L)-(+)-Diethyl tartarate 2 has been transformed into the aldehyde 6. Grignard additions to 6 take place with moderate diastereoselectivity giving predominant formation of the anti products 8a-e. However, in ea ch case the diastereoalcohols are easily separable by column chromatog raphy giving rise to the formation of a series of functionalised homoc hiral alcohols 7 and 8. On the other hand Zn mediated allylation and p ropargylation of 6 in the presence of water proceeded efficiently with almost absolute (>99%) stereoselective formation of versatile functio nalised homoallylic 8d and homopropargylic 8e alcohols respectively. ( C) 1998 Elsevier Science Ltd. All rights reserved.