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Bispidine-derived N-acyliminium ions in synthesis: stereocontrolled construction of the BCD rings of sparteine

✍ Scribed by Justin R Harrison; Peter O'Brien

Book ID: 104210629
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 154 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00999-0

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✦ Synopsis

Reaction of Grignard reagents with bispidine-derived N-acyliminium ions (generated in situ from an amethoxy bispidine amide) has been studied as a new route to sparteine analogues. The addition reactions proceed with complete diastereoselectivity to generate products with the same relative stereochemistry as in the BCD rings of sparteine. The ®rst stereocontrolled synthesis of a tricyclic diamine structurally equivalent to the BCD rings of sparteine, is described.

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