Cooperative Pd/Chiral Secondary Amine Enabled Diastereo- and Enantioselective [3 + 2] Cycloannulation: Synthesis of Polysubstituted Cyclopentanes

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-17 DOI:10.1021/acs.orglett.5c00007

Zuoqin Luo, Limei Gao, Dongqing He, Yuting Tian, Jikai Liu, Yongsheng Zheng

引用次数: 0

Abstract

A cooperative palladium/chiral amine enabled diastereo- and enantioselective [3 + 2] cycloaddition of π-allyl 1,3-dipoles with α,β-unsaturated aldehydes has been developed. A series of highly functionalized cyclopentanes bearing three continuous tertiary stereocenters can be facilely and efficiently obtained in good to excellent yields (51–97%) with synthetically useful diastereo- and enantioselectivity (93–99% ee) under mild reaction conditions. Control experiments and HRMS analyses were conducted to elucidate the possible mechanism. The utility of the current method was demonstrated by the gram-scale synthesis and elaboration of the products into various functionalized cyclopentanes.

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Pd/手性仲胺协同非对映和对映选择性[3 + 2]环环：多取代环戊烷的合成

研究了钯/手性胺使π-烯丙基1,3偶极子与α，β-不饱和醛的非对映和对映选择性[3 + 2]环加成反应。在温和的反应条件下，一系列具有三个连续叔立体中心的高官能化环戊烷可以以良好的收率（51-97%）和合成有用的非对映和对映选择性（93-99% ee）得到。通过对照实验和HRMS分析来阐明可能的机理。通过克级合成并将产物精制成各种功能化环戊烷，证明了该方法的实用性。

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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.