Chemical Dynamic Thermodynamic Resolution and S/R Interconversion of Unprotected Unnatural Tailor-made 伪-Amino Acids
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- 作者：Shuni Wang ; Shengbin Zhou ; Jiang Wang ; Yong Nian ; Aki Kawashima ; Hiroki Moriwaki ; Jos茅 L. Ace帽a ; Vadim A. Soloshonok ; Hong Liu
- 刊名：Journal of Organic Chemistry
- 出版年：2015
- 出版时间：October 16, 2015
- 年：2015
- 卷：80
- 期：20
- 页码：9817-9830
- 全文大小：659K
- ISSN：1520-6904
文摘
Described here is an advanced, general method for purely chemical dynamic thermodynamic resolution and S/R interconversion of unprotected tailor-made 伪-amino acids (伪-AAs) through intermediate formation of the corresponding nickel(II)-chelated Schiff bases. The method features virtually complete stereochemical outcome, broad substrate generality (35 examples), and operationally convenient conditions allowing for large-scale preparation of the target 伪-AAs in enantiomerically pure form. Furthermore, the new type of nonracemizable axially chiral ligands can be quantitatively recycled and reused, rendering the whole process economically and synthetically attractive.