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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Veröffentlicht in:Journal of the American Chemical Society 2011-06, Vol.133 (22), p.8428-8431
Hauptverfasser: 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
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Sprache:eng
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Zusammenfassung: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja201589k