Stereoselective Synthesis of 2-Substituted Pyrrolidines
- 1 January 2000
- journal article
- Published by Institute of Organic Chemistry & Biochemistry in Collection of Czechoslovak Chemical Communications
- Vol. 65 (5) , 816-828
- https://doi.org/10.1135/cccc20000816
Abstract
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.Keywords
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