Stereoselective synthesis of new beta-lactams by cyclocondensation of 1-methoxy-3-(trimethylsilyloxy)-1,3-butadiene with 4-formyl substituted azetidinones

R Annunziata; M Benaglia; M Cinquini; F Cozzi; F Montanari; L Raimondi

doi:10.1016/s0014-827x(98)00077-9

Stereoselective synthesis of new beta-lactams by cyclocondensation of 1-methoxy-3-(trimethylsilyloxy)-1,3-butadiene with 4-formyl substituted azetidinones

Farmaco. 1998 Oct-Nov;53(10-11):629-33. doi: 10.1016/s0014-827x(98)00077-9.

Authors

R Annunziata¹, M Benaglia, M Cinquini, F Cozzi, F Montanari, L Raimondi

Affiliation

¹ Centro CNR, Universitá degli Studi di Milano, Italy.

PMID: 10205849
DOI: 10.1016/s0014-827x(98)00077-9

Abstract

The BF3.OEt2 or LiClO4 catalyzed hetero Diels-Alder reaction of 1-methoxy-3-(trimethylsilyloxy)-1,3-butadiene (Danishefsky's diene) with enantiomerically pure 4-formylazetidin-2-ones affords the corresponding cycloadducts in fair to good yields and in diastereoisomeric ratios of up to 98:2.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Azetidines / chemistry*
Butadienes / chemistry*
Stereoisomerism
beta-Lactams

Substances

Anti-Bacterial Agents
Azetidines
Butadienes
beta-Lactams