Chiral Phosphoric Acid-Catalyzed Addition of Thiols to N-Acyl Imines: Access to Chiral N,S-Acetals

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2011-08-15 DOI:10.1021/ol201899c

Gajendrasingh K. Ingle, Michael G. Mormino, Lukasz Wojtas, Jon C. Antilla

引用次数: 68

Abstract

The first catalytic asymmetric method to prepare enantioenriched N,S-acetals using chiral BINOL phosphoric acids is reported. The reaction combines N-acyl imines with thiols to generate products in excellent yield and enantioselectivity. The addition reaction could also be achieved with an exceptional substrate to catalyst (S/C) molar ratio. Electron-rich and electron-deficient aromatic N-acyl imines, as well as a broad range of aliphatic and aromatic thiols, showed excellent reactivity.

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手性磷酸催化巯基加成到N-酰基亚胺:获得手性N, s -缩醛

报道了首次用手性二醇磷酸催化不对称法制备富对映体N, s -缩醛的方法。该反应将n -酰基亚胺与硫醇结合，生成收率高、对映选择性好的产物。当底物与催化剂(S/C)的摩尔比特殊时，加成反应也可以实现。富电子和缺电子芳香n-酰基亚胺以及多种脂肪族和芳香硫醇均表现出优异的反应活性。

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

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.