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The Stereochemistry of Carbenoid Cyclopropanation Reactions

✍ Scribed by Hans Christian Stiasny; Reinhard W. Hoffmann

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
670 KB
Volume
1
Category
Article
ISSN
0947-6539

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✦ Synopsis

The stereochemical course of the intramolecular carbenoid cyclopropanation reaction has been studied for the epimeric carbenoids 12a and 12b. In these reactions the terl-butyldimethylsilyloxy substituent serves as an internal stereochemical reference point. It was found that 12b cyclizes rapidly at -110Β°C in a complexation-assisted concerted process to give the bicyclo[3.1 .O]hexane 16. The diastereomer 12a cyclizes more slowly at -100 "C to give both 16 and 17; the former IS probably formed by a complexation-assisted carbolithiation pathway.

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