Diastereoselectively Switchable Enantioselective Trapping of Carbamate Ammonium Ylides with Imines

Diastereoselectively Switchable Enantioselective Trapping of Carbamate Ammonium Ylides with Imines

The diastereoselectively switchable enantioselective trapping of protic carbamate ammonium ylides with imines is reported. The intriguing Rh2(OAc)4 and chiral Brønsted acid cocatalyzed three-component Mannich-type reaction of a diazo compound, a carbamate, and an imine provides rapid and efficient a...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 133; no. 22; pp. 8428 - 8431
Main Authors: Jiang, Jun, Xu, Hua-Dong, Xi, Jian-Bei, Ren, Bai-Yan, Lv, Feng-Ping, Guo, Xin, Jiang, Li-Qin, Zhang, Zhi-Yong, Hu, Wen-Hao
Format: Journal Article
Language:English
Published: United States American Chemical Society 08-06-2011
Subjects:
Carbamates - chemistry
Catalysis
Imines - chemistry
Molecular Structure
Phosphoric Acids - chemistry
Quaternary Ammonium Compounds - chemistry
Rhodium - chemistry
Stereoisomerism
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Summary:The diastereoselectively switchable enantioselective trapping of protic carbamate ammonium ylides with imines is reported. The intriguing Rh2(OAc)4 and chiral Brønsted acid cocatalyzed three-component Mannich-type reaction of a diazo compound, a carbamate, and an imine provides rapid and efficient access to both syn- and anti-α-substituted α,β-diamino acid derivatives with a high level control of chemo-, diastereo-, and enantioselectivity.
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja201589k