Stereoselective [1,2]-Phospha-Brook Rearrangement of CAMDOL-Derived H-Phosphonate: Synthesis of α-Trifluoromethyl Alcohols

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-01 DOI:10.1021/acs.orglett.5c00686

Ning Li, Qian Wu, Yu Huang, Junchen Li, Enxue Shi

引用次数: 0

Abstract

A highly efficient and stereoselective [1,2]-phospha-Brook rearrangement of fluoromethyl ketones has been achieved by utilizing a new type of P-chiral H-phosphonate derived from CAMDOL, designated as CAMDOL-PHO. A library of 38 secondary alcohols featuring an α-trifluoromethyl or trifluoroaryl motif were afforded in up to 97% yield with 99:1 dr. Compared to other known chiral auxiliaries, bicyclic CAMDOL exhibits superior induction ability due to its unique center-chiral scaffold.

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camdoll衍生h -膦酸盐的立体选择性[1,2]-Phospha-Brook重排：α-三氟甲基醇的合成

利用CAMDOL衍生的一种新型p手性h -膦酸盐（CAMDOL- pho），实现了氟甲基酮的高效立体选择性[1,2]-磷酸-布鲁克重排。以α-三氟甲基基或三氟芳基基为基序的仲醇共38个，产率高达97%，收率为99:1 dr.与其他已知的手性助剂相比，双环CAMDOL由于其独特的中心手性支架而具有优越的诱导能力。

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.