Stereoselective Synthesis of 2-Substituted Pyrrolidines

6533b826fe1ef96bd1284ee6

RESEARCH PRODUCT

Stereoselective Synthesis of 2-Substituted Pyrrolidines

Sandrine Deloisy Heiko Tietgen Horst Kunz

subject

chemistry.chemical_classification Aldimine Nornicotine chemistry.chemical_compound Chemistry Diastereomer Stereoselectivity General Chemistry Medicinal chemistry

description

Using O-pivaloyl protected D-galactopyranosylamine and D-arabinopyranosylamine, (S) or (R) configured α-substituted homoallylamines are synthesized with high diastereoselectivity by reaction of the corresponding aldimines with allyltributylstannane. Electrophile-induced endo-trig-cyclization of these N-glycosylhomoallylamines gave the 2-substituted pyrrolidines of high diastereomeric purity.

year	journal	country	edition	language
2000-01-01	Collection of Czechoslovak Chemical Communications

https://doi.org/10.1135/cccc20000816

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