Premium
A New Access to Enantiopure syn ‐ and anti ‐2‐Methyl‐1,3‐diol Moieties from Chiral Nonracemic α‐Bromo α′‐Sulfinyl Ketones Promoted by Samarium Diiodide
Author(s) -
Colobert Françoise,
Obringer Michel,
Solladié Guy
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500782
Subject(s) - enantiopure drug , chemistry , stereoselectivity , stereochemistry , diol , aldehyde , sulfoxide , reformatsky reaction , adduct , enantioselective synthesis , absolute configuration , total synthesis , organic chemistry , catalysis
syn‐ and anti ‐2‐Methyl‐1,3‐diols have been prepared by a two‐step sequence that involves a SmI 2 ‐promoted stereoselective Reformatsky addition of chiral nonracemic α‐bromo α′‐sulfinyl ketones to various aldehydes followed by stereoselective reduction of the Reformatsky adduct. The absolute configuration of the products was determined by comparison with literature data and by 1 H NMR NOESY experiments. The observed stereoselectivities can be explained in terms of a boat transition state. Functionalization of the aldehyde and removal or transformation of the chiral sulfoxide will allow this methodology to be applied to the total synthesis of biologically active molecules. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)