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