通过手性N-叔丁基亚磺酰亚胺酯合成天冬氨酸衍生物的不对称曼尼希型反应。
Asymmetric Mannich-type reactions for the synthesis of aspartic acid derivatives from chiral N-tert-butanesulfinylimino esters.
作者信息
Jacobsen Mikkel F, Skrydstrup Troels
机构信息
Department of Chemistry, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark.
出版信息
J Org Chem. 2003 Sep 5;68(18):7112-4. doi: 10.1021/jo034436j.
PMID:12946161
Abstract
Addition of ketene acetals to sulfinimines derived from homochiral N-tert-butanesulfinamide using various Lewis acids furnishes derivatives of aspartic acid in diastereomeric ratios up to 97:3. Following an easy removal of the N-tert-butanesulfinyl chiral auxiliary, optical active beta-amino esters are obtained.
摘要
使用各种路易斯酸将乙烯酮缩醛添加到源自同手性N-叔丁基亚磺酰胺的亚磺酰亚胺中，可得到非对映体比例高达97:3的天冬氨酸衍生物。在轻松除去N-叔丁基亚磺酰基手性助剂后，可得到光学活性的β-氨基酯。
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