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Asymmetric Synthesis of Polyfunctionalized Pyrrolidines and Related Alkaloids

✍ Scribed by Stephen G. Pyne; Andrew S. Davis; Nicole J. Gates; Joseph P. Hartley; Karl B. Lindsay; Theeraphan Machan; Minyan Tang

Publisher
John Wiley and Sons
Year
2005
Weight
8 KB
Volume
36
Category
Article
ISSN
0931-7597

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ChemInform Abstract: Asymmetric Routes T
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Starting from the (R)-(-)-phenylglycinol derivative (I), the stereoselective synthesis of polyhydroxylated pyrrolidines [cf. (VIII)] and the indolizidine (XII) is based on the diastereoselective condensation of the chiral silyloxypyrrole (III) with aldehydes (IV). The preparation of the indolizidine

Asymmetric Synthesis of Polyfunctionaliz
Asymmetric Synthesis of Polyfunctionalized Pyrrolidines via a Thiourea Catalyzed Domino Mannich/Aza-Michael Reaction
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## Abstract The domino Mannich/aza‐Michael reaction of γ‐malonate‐substituted α,β‐unsaturated esters with __N__‐protected arylaldimines has been achieved. Catalyzed by bifunctional thioureas, 2,5‐__cis__‐configured polysubstituted pyrrolidines are obtained in good to excellent yields (76–99%), enan