Highly diastereoselective Michael additions onto dienyl bis-sulfoxides

An optimized procedure for the preparation of (S-s,S-s)-bis(p-tolylsulfinyl)methane (4) is reported. Condensation of the lithium salt of 4 onto cinnamaldehyde furnished bis-sulfoxide dienyl derivative 5, a remarkable 1,4-Michael acceptor that can lead in a highly diastereoselective manner to vinyley...

Full description

Saved in:
Bibliographic Details
Published inSynthesis (Stuttgart) no. 14; pp. 2449 - 2452
Main Authors Brebion, F, Goddard, JP, Fensterbank, L, Malacria, M
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 02.09.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Michael addition
bis-sulfoxide
ASYMMETRIC-SYNTHESIS
cryptophycin
REACTIVITY
vinylcyclopropane
BIS(SULFOXIDES)
Online AccessGet more information

Cover

More Information
Summary:An optimized procedure for the preparation of (S-s,S-s)-bis(p-tolylsulfinyl)methane (4) is reported. Condensation of the lithium salt of 4 onto cinnamaldehyde furnished bis-sulfoxide dienyl derivative 5, a remarkable 1,4-Michael acceptor that can lead in a highly diastereoselective manner to vinyleyclopropyl adducts. In a chelating mode of reactivity using a methylcopper reagent, a complete reversal of stereoselectivity is observed giving an enantiopure beta,gamma-unsaturated methyl ester intermediate that is used in the synthesis of cryptophycin.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2005-872089