A New Synthesis of Pyrrolidines by Way of an Enantioselective Mannich/Diastereoselective Hydroamination Reaction Sequence

A new two-step synthesis of highly substituted pyrrolidines has been developed. Chiral silane Lewis acid promoted enantioselective Mannich reactions of silyl ketene imines with acylhydrazones may be used to access bishomoallylic benzoic hydrazides that in turn may be cyclized to pyrrolidines by way...

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Bibliographic Details
Published in:Organic letters 2011-08, Vol.13 (15), p.4056-4059
Main Authors: Baxter Vu, Jenny M, Leighton, James L
Format: Article
Language:English
Subjects:
Amination
Cyclization
Hydrogen - chemistry
Molecular Structure
Pyrrolidines - chemical synthesis
Stereoisomerism
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Summary:A new two-step synthesis of highly substituted pyrrolidines has been developed. Chiral silane Lewis acid promoted enantioselective Mannich reactions of silyl ketene imines with acylhydrazones may be used to access bishomoallylic benzoic hydrazides that in turn may be cyclized to pyrrolidines by way of the thermal hydroamination reaction reported recently by Beauchemin. Importantly, excellent diastereoselectivity may be realized in the hydroamination reactions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201566u