Enantio- and Regioselective Propargylation and Allenylation of β,γ-Unsaturated α-Ketoesters with Allenyl Boronate Regulated by Chiral Copper/Zinc

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-01-31 DOI:10.1021/acs.orglett.4c0384510.1021/acs.orglett.4c03845

Shuai-Ru Cheng, Ni Zhao, Wei Ma, Guo-Rong Ma and Pei Wang*,

引用次数: 0

Abstract

A method for asymmetric propargylation and allenylation of β,γ-unsaturated α-ketoesters catalyzed by Box-Cu/Box-Zn using a commercial organoboron reagent is reported. The reaction was demonstrated to be broadly tolerant of functional groups, resulting in a series of propargyl and allenyl tertiary alcohols in excellent yields with high enantio- and regioselectivities. Furthermore, the proposed mechanism was supported by density functional theory calculations. Gram-scale experiments as well as the synthesis of various chiral tertiary alcohols and glycol derivatives demonstrated the practicality of this synthetic strategy.

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手性铜/锌调控β，γ-不饱和α-酮酯与硼烯酸丙烯基的对映和区域选择性丙烯基化

报道了Box-Cu/Box-Zn在商用有机硼试剂上催化β，γ-不饱和α-酮酯的不对称丙基化和烯丙化反应。该反应被证明对官能团具有广泛的耐受性，产生一系列具有高对映性和区域选择性的丙炔基和烯基叔醇。此外，密度泛函理论计算也支持了上述机理。克级实验以及各种手性叔醇和乙二醇衍生物的合成证明了这种合成策略的实用性。

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.