Azetidin-2,3-dione Synthon for Stereoselective Synthesis of cis- and trans-C-3-Alkyl/Aryl Azetidin-2-ones

Dharmendra Kumar Tiwari; Vikas K. Gumaste; Abdul Rakeeb A. S. Deshmukh

doi:10.1055/s-2005-921746

PAPER

Azetidin-2,3-dione Synthon for Stereoselective Synthesis of cis- and trans-C-3-Alkyl/Aryl Azetidin-2-ones

Dharmendra Kumar Tiwari, Vikas K. Gumaste, Abdul Rakeeb A. S. Deshmukh*
Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India
Fax: +91(20)25893153; Fax: +91(20)25893355; e-Mail: aras.deshmukh@ncl.res.in;

Abstract

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Abstract

1,4-Bis-(4-methoxyphenyl)azetidin-2,3-dione has been prepared and used as a synthon for the stereoselective synthesis of C-3-alkyl/aryl azetidin-2-ones. Some of these are well known for their cholesterol absorption inhibitor activity. A regioselective Grignard reaction at a keto-group followed by highly stereoselective removal of the hydroxyl group via reductive removal of the xanthate ester is a key step in this synthesis. Base-induced isomerization of cis-azetidin-2-ones to the thermodynamically stable trans-isomer was also studied.

Keywords

azetidin-2,3-diones - azetidin-2-ones - β-lactam - Grignard reaction - tributyltin hydride

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