铜催化的碘𬭩叶立德的对映选择性、非对映选择性和区域选择性[2,3]-重排。
Copper-Catalyzed Enantio-, Diastereo-, and Regioselective [2,3]-Rearrangements of Iodonium Ylides.
机构信息
Department of Biochemistry, The University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, TX, 75390-9038, USA.
出版信息
Angew Chem Int Ed Engl. 2017 Aug 7;56(33):9868-9871. doi: 10.1002/anie.201705317. Epub 2017 Jul 17.
Abstract
The first highly enantioselective, diastereoselective, and regioselective [2,3]-rearrangement of iodonium ylides has been developed as a general solution to catalytic onium ylide rearrangements. In the presence of a chiral copper catalyst, substituted allylic iodides couple with α-diazoesters to generate metal-coordinated iodonium ylides, which undergo [2,3]-rearrangements with high selectivities (up to >95:5 r.r., up to >95:5 d.r., and up to 97 % ee). The enantioenriched iodoester products can be converted stereospecifically into a variety of onium ylide rearrangement products, as well as compounds that are not accessible by classical onium ylide rearrangements.
摘要
首次发展了高对映选择性、非对映选择性和区域选择性的[2,3]-重排碘𬭩叶立德反应，作为催化氧𬭩叶立德重排的通用方法。在手性铜催化剂的存在下，取代的烯丙基碘与α-重氮酯偶联生成金属配位的碘𬭩叶立德，它们以高选择性（高达>95:5 r.r.，高达>95:5 d.r.，高达 97%ee）进行[2,3]-重排。手性碘酯产物可以立体专一性转化为各种氧𬭩叶立德重排产物，以及通过经典氧𬭩叶立德重排无法获得的化合物。
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