Enantioselective Synthesis of α‐Trifluoromethyl tert‐Alcohols and Amines via Organocatalyst‐Mediated Aldol and Mannich Reactions

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2025-04-01 DOI:10.1002/ajoc.202500035

Yujiro Hayashi , Hinata Odaira , Masashi Tomikawa , Naoki Mori , Tohru Taniguchi , Kenji Monde

引用次数: 0

Abstract

The asymmetric aldol reaction of ethyl trifluoropyruvate with aldehydes was developed using diarylprolinol as a catalyst, affording α‐trifluoromethyl‐substituted tertiary alcohols with high enantioselectivity. Similarly, the asymmetric Mannich reaction of aldehydes with an imine derived from ethyl trifluoropyruvate was developed using diphenylprolinol silyl ether in combination with an acid, yielding α‐trifluoromethyl‐substituted tertiary amines. The absolute and relative configurations of the products were determined by vibrational circular dichroism (VCD).

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有机催化剂介导的Aldol和Mannich反应对映选择性合成α-三氟甲基叔醇和胺

以二芳基脯氨酸为催化剂，研究了三氟丙酮酸乙酯与醛的不对称醛醇反应，得到了具有高对映选择性的α-三氟甲基取代叔醇。同样，用二苯基脯氨醇硅基醚与一种酸结合，开发了醛与三氟丙酮酸乙酯衍生的亚胺的不对称曼尼希反应，得到α-三氟甲基取代叔胺。用振动圆二色性（VCD）测定了产物的绝对构型和相对构型。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.