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Addition of a Chiral Boron Enolate to Cyclic N -Acyliminium Ions. Stereocontrolled Synthesis of the Pyrrolizidine Ring System

โœ Scribed by Pilli, Ronaldo A.; Russowsky, Dennis


Book ID
127343252
Publisher
American Chemical Society
Year
1996
Tongue
English
Weight
224 KB
Volume
61
Category
Article
ISSN
0022-3263

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The vinylogous Mannich addition of silyloxyfuran 5 to chiral five-and six-membered N-acyliminium ions derived from 3/4a,b occurred exclusively through the addition to the N-acyliminium Si face to provide threo-6/7a,b as the major isomer (73-84% yield, 2:1-7:1 diastereoisomeric ratio) which were conv