Studies Toward Improved Enantiocontrol in the Asymmetric Cu-Catalyzed Reductive Coupling of Ketones and Allenamides: 1,2-Aminoalcohol Synthesis

被引：8

作者：

Collins, Stephen ^{[1
]}

Sieber, Joshua D. ^{[1
]}

机构：

[1] Virginia Commonwealth Univ, Dept Chem, Richmond, VA 23284 USA

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 09期

基金：

美国国家科学基金会;

关键词：

STEREOSELECTIVE-SYNTHESIS; NATURAL-PRODUCTS; ALCOHOLS; STEREOCHEMISTRY; ALLYLATION; ALDEHYDES; REAGENTS; ALLENES; IMINES;

D O I：

10.1021/acs.orglett.3c00157

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report the development of an improved system for the Cu-catalyzed enantioselective reductive coupling of ketones and allenamides through the optimization of the allenamide to avoid an on-cycle rearrangement. High enantioselectivities could be obtained for a variety of ketones. Use of the acyclic allenamides described herein selectively generated anti-diastereomers in contrast to cyclic allenamides that were previously shown to favor the syn-form. A rationale for this change in diastereoselectivity is also presented.

引用

页码：1425 / 1430

页数：6

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