Stereoselective synthesis of 3-alkylidene/alkylazetidin-2-ones from azetidin-2,3-diones

TY - JOUR

T1 - Stereoselective synthesis of 3-alkylidene/alkylazetidin-2-ones from azetidin-2,3-diones

AU - Tiwari, Dharmendra Kumar

AU - Shaikh, Ashif Y.

AU - Pavase, Laxmikant S.

AU - Gumaste, Vikas K.

AU - Deshmukh, Abdul Rakeeb A S

PY - 2007/3/12

Y1 - 2007/3/12

N2 - Azetidin-2,3-diones have been used as synthons for the synthesis of C-3 alkylidene/alkylazetidin-2-ones. Some of the 3-alkylazetidin-2-ones are well known for their cholesterol absorption inhibitor activity. A regio and stereoselective Grignard reaction on a keto group followed by dehydration using PPh3/CCl4 reagent is a key step in this synthesis. Hydrogenation of the 3-alkylideneazetidin-2-ones provided stereoselectively cis-3-alkylazetidin-2-ones in very good yields.

AB - Azetidin-2,3-diones have been used as synthons for the synthesis of C-3 alkylidene/alkylazetidin-2-ones. Some of the 3-alkylazetidin-2-ones are well known for their cholesterol absorption inhibitor activity. A regio and stereoselective Grignard reaction on a keto group followed by dehydration using PPh3/CCl4 reagent is a key step in this synthesis. Hydrogenation of the 3-alkylideneazetidin-2-ones provided stereoselectively cis-3-alkylazetidin-2-ones in very good yields.

KW - β-Lactam

KW - Azetidin-2,3-diones

KW - Azetidin-2-ones

KW - Grignard reaction

UR - http://www.scopus.com/inward/record.url?scp=33846813846&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2006.12.010

DO - 10.1016/j.tet.2006.12.010

M3 - Journal article

AN - SCOPUS:33846813846

SN - 0040-4020

VL - 63

SP - 2524

EP - 2534

JO - Tetrahedron

JF - Tetrahedron

IS - 11

ER -