联萘酚锂催化丙二酸酯与马来酸酯的迈克尔反应及其在三羧酸衍生物对映选择性合成中的应用

Lithium Binaphtholate-Catalyzed Michael Reaction of Malonates with Maleates and Its Application to the Enantioselective Synthesis of Tricarboxylic Acid Derivatives.

作者信息

Sakamoto Midori, Kaneko Tetsuya, Orito Yuya, Shimoda Yasushi, Nakajima Makoto

机构信息

Graduate School of Pharmaceutical Sciences, Kumamoto University.

出版信息

Chem Pharm Bull (Tokyo). 2019;67(5):452-460. doi: 10.1248/cpb.c18-00993.

DOI:10.1248/cpb.c18-00993

PMID:31061370

Abstract

The Michael reaction of malonates with maleates afforded the corresponding adducts in high yields with high enantioselectivities (up to 98% enantiomeric excess (ee)) by using dilithium 3,3'-dichlorobinaphtholate as a catalyst. The obtained Michael adducts could be converted to optically active tricarboxylic acid (TCA) derivatives via the Krapcho reaction.

摘要

通过使用3,3'-二氯联萘酚二锂作为催化剂，丙二酸酯与马来酸酯的迈克尔反应以高收率和高对映选择性（对映体过量高达98%）得到相应的加合物。所得到的迈克尔加合物可通过克拉普乔反应转化为光学活性的三羧酸（TCA）衍生物。