Highly Stereocontrolled Cyclopropanation by the 1,3-Elimination of a Bis(tributylstannyl)propanol Derivative

The highly stereoselective ring closure of γ-hydroxystannyl derivative was realized. The aldol reaction of methyl bis(tributylstannyl)propionate (2) with aldehyde 5 proceeds stereoselectively to give (γ-hydroxypropyl)stannane 6, and the cyclopropanation reaction of aldol product 6 proceeds smoothly...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 1996-11, Vol.61 (22), p.7867-7872
Main Authors: Isono, Naohiro, Mori, Miwako
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The highly stereoselective ring closure of γ-hydroxystannyl derivative was realized. The aldol reaction of methyl bis(tributylstannyl)propionate (2) with aldehyde 5 proceeds stereoselectively to give (γ-hydroxypropyl)stannane 6, and the cyclopropanation reaction of aldol product 6 proceeds smoothly in a highly stereoselective manner presumably via a W-shape transition state. The stannyl group on the cyclopropane ring can be converted into various electrophiles with a retention of configuration. As a result, various stereocontrolled 1,2,3-trisubstituted cyclopropanes can be obtained in high yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo960981r