用于酮与羰基化合物不对称交叉羟醛反应的新型硼氨基酰胺有机催化剂。

New boro amino amide organocatalysts for asymmetric cross aldol reaction of ketones with carbonyl compounds.

作者信息

Begum Zubeda, Seki Chigusa, Okuyama Yuko, Kwon Eunsang, Uwai Koji, Tokiwa Michio, Tokiwa Suguru, Takeshita Mitsuhiro, Nakano Hiroto

机构信息

Division of Sustainable and Environmental Engineering, Graduate School of Engineering, Muroran Institute of Technology 27-1 Mizumoto-cho Muroran 050-8585 Japan

Tohoku Medical and Pharmaceutical University 4-4-1 Komatsushima, Aoba-Ku Sendai 981-8558 Japan.

出版信息

RSC Adv. 2023 Jan 4;13(2):888-894. doi: 10.1039/d2ra06272k. eCollection 2023 Jan 3.

DOI:10.1039/d2ra06272k

PMID:36686933

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9811241/

Abstract

Distinct types of new boron fused primary amino amide organocatalysts were designed and synthesized from commercially available amino acids. Their catalytic activities were investigated in asymmetric crossed aldol reaction of ketones with aromatic aldehydes to afford the corresponding chiral -aldol adducts with good chemical yields, moderate diastereoselectivity and good to excellent enantioselectivities (up to 94% yields, up to 90 : 10 dr, up to 94% ee).

摘要

从市售氨基酸出发，设计并合成了不同类型的新型硼稠合伯氨基酰胺有机催化剂。研究了它们在酮与芳香醛的不对称交叉羟醛反应中的催化活性，以良好的化学产率、适度的非对映选择性和良好至优异的对映选择性（产率高达94%，非对映体比例高达90:10，对映体过量高达94%）得到相应的手性羟醛加合物。