Organocatalytic Enantioselective Mannich-Type Reaction of Phosphorus Ylides:  Synthesis of Chiral N-Boc-β-Amino-α-methylene Carboxylic Esters

The first asymmetric Mannich-type reaction of stabilized phosphorus ylides and N-Boc aldimines was described promoted by a readily available and recyclable chiral bisthiourea organocatalyst. Subsequent reaction with formalin smoothly provides N-Boc-β-amino-α-methylene carboxylic esters in a highly e...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2008-02, Vol.130 (8), p.2456-2457
Main Authors: Zhang, Yan, Liu, Yan-Kai, Kang, Tai-Ran, Hu, Ze-Kai, Chen, Ying-Chun
Format: Article
Language:English
Subjects:
Carboxylic Acids - chemical synthesis
Carboxylic Acids - chemistry
Catalysis
Esters - chemical synthesis
Esters - chemistry
Molecular Structure
Phosphines - chemistry
Stereoisomerism
Thiourea - analogs & derivatives
Thiourea - chemistry
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Summary:The first asymmetric Mannich-type reaction of stabilized phosphorus ylides and N-Boc aldimines was described promoted by a readily available and recyclable chiral bisthiourea organocatalyst. Subsequent reaction with formalin smoothly provides N-Boc-β-amino-α-methylene carboxylic esters in a highly enantiomerically enriched form (up to 96% ee).
ISSN:0002-7863
1520-5126
DOI:10.1021/ja7114844