Pd-Catalyzed Asymmetric Annulative Dearomatization of Phenols for Regio- and Enantioselective Synthesis of Spirocyclohexadienones

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2023-08-04 DOI:10.1021/acs.orglett.3c02051

Hui-Lin Mao, Yu-Xin Wang, Xue Wang, Hai-Ying Wang*, Wen-Juan Hao* and Bo Jiang*,

引用次数: 0

Abstract

A palladium-catalyzed asymmetric annulative dearomatization of phenols with butene dicarbonate is reported, enabling twofold decarboxylative allylation to regioselectively produce a range of spirocyclohexadienones with 29–95% yields and 74–99% ee. A catalytic dearomative formal [4 + 2] cyclization of 1,1′-biphenyl-2,4′-diols delivered spiro[chromane-4,1′-cyclohexane]-2′,5′-dien-4′-ones with high enantioselectivity, whereas enantioenriched spiro[cyclohexane-1,4′-quinoline]-2,5-dien-4-ones were generated starting from 2′-amino-[1,1′-biphenyl]-4-ols as 1,4-dinucleophiles.

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邻环己二烯酮在pd催化下的不对称环性脱芳化反应

报道了钯催化苯酚与二碳酸丁烯的不对称环化脱芳反应，使双重脱羧烯丙基化能够区域选择性地产生一系列的螺环己二烯酮，收率为29-95%，ee为74-99%。对1,1 ' -联苯-2,4 ' -二醇进行催化脱芳[4 + 2]环化反应，产生具有高对映选择性的螺[铬-4,1 ' -环己烷]-2 '，5 ' -二烯-4 ' -1 -酮，而对映富集的螺[环己烷-1,4 ' -喹啉]-2,5-二烯-4-酮则由2 ' -氨基-[1,1 ' -联苯]-4-醇作为亲1,4-二核试剂生成。

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.