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- Title
Stereoselective Lewis Base-Catalyzed Asymmetric Hydrosilylation of α-Acetamido-β-enamino Esters: Straightforward Approach for the Construction of α,β-Diamino Acid Derivatives.
- Authors
Jiang, Yan; Chen, Xing; Hu, Xiao ‐ Yan; Shu, Chang; Zhang, Yong ‐ Hong; Zheng, Yong ‐ Sheng; Lian, Chun ‐ Xia; Yuan, Wei ‐ Cheng; Zhang, Xiao ‐ Mei
- Abstract
The Lewis base-organocatalyzed asymmetric hydrosilylation of α-acetamido-β-enamino esters was investigated. Among various chiral Lewis base catalysts, a novel catalyst derived from L-serine was found to be the most efficient one which can promote the reaction to afford a series of α,β-diamino acid derivatives with high yields (up to 99%), excellent enantioselectivities (up to 98% ee) and moderate diastereoselectivities (up to 80:20 dr). The absolute configuration of one of the products was determined by the X-ray crystallographic analysis. In addition, the mechanism and the transition state of the reaction were proposed.
- Subjects
CHEMICAL synthesis; ESTERS; ASYMMETRIC synthesis; STEREOSELECTIVE reactions; LEWIS bases; HYDROSILYLATION; AMINO acid derivatives
- Publication
Advanced Synthesis & Catalysis, 2013, Vol 355, Issue 10, p1931
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201300184