Chiral Silver Amide-Catalyzed Enantioselective [3 + 2] Cycloaddition of α-Aminophosphonates with Olefins

The first catalytic asymmetric [3 + 2] cycloadditions of Schiff bases of α-aminophosphonates with olefins have been developed. Chiral silver amide complexes bearing (R)-DTBM-SEGPHOS worked well as catalysts for the first time, and proline phosphonic analogues were obtained in high yields with excell...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2010-03, Vol.132 (10), p.3262-3263
Main Authors: Yamashita, Yasuhiro, Guo, Xun-Xiang, Takashita, Ryuta, Kobayashi, Shu̅
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Amides - chemistry
Amines - chemistry
Catalysis
Cyclization
Organomercury Compounds - chemistry
Organophosphonates - chemistry
Proline - analogs & derivatives
Proline - chemical synthesis
Schiff Bases - chemistry
Silver - chemistry
Stereoisomerism
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Summary:The first catalytic asymmetric [3 + 2] cycloadditions of Schiff bases of α-aminophosphonates with olefins have been developed. Chiral silver amide complexes bearing (R)-DTBM-SEGPHOS worked well as catalysts for the first time, and proline phosphonic analogues were obtained in high yields with excellent exo- and enantioselectivities.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja100101n