Cu(I)/Chiral Bisoxazoline-Catalyzed Enantioselective Doyle-Kirmse Reaction of Allenyl Sulfides with alpha-Diazoesters
Cu(I)/Chiral Bisoxazoline-Catalyzed Enantioselective Doyle-Kirmse Reaction of Allenyl Sulfides with alpha-Diazoesters
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Cu(I)/手性双恶唑啉催化烯基硫醚与 α-重氮酯的对映选择性 Doyle-Kirmse 反应
DOI：
10.1002/chem.202200170
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发表时间：
2022
期刊：
影响因子：
--
通讯作者：
Jianbo Wang
中科院分区：
文献类型：
--
作者：
Kang Wang;Shu-Sen Li;Jianbo Wang
本文报道了Cu（I）催化的丙二烯基硫醚与α-重氮酯的不对称Doyle-Kirmse反应，该反应为合成手性高炔丙基硫醚提供了一条有效的途径。该反应具有高的对映选择性（高达96%ee）和良好的官能团耐受性.烷基取代的α-重氮酯也被证明是不对称Doyle-Kirmse反应的有效底物。进行了包括动力学实验在内的机理研究，以深入了解反应途径的细节。该协议的潜在的合成效用也已被证明。
Herein, a Cu(I)-catalyzed enantioselective Doyle-Kirmse reaction of allenyl sulfides and α-diazoesters is reported, which provides an efficient synthetic route to enantio-enriched chiral tertiary homopropargylic sulfides. This reaction features high enantioselectivities (up to 96 % ee) and good functional group tolerance. The alkyl substituted α-diazoester has also been demonstrated as the efficient substrates in the asymmetric Doyle-Kirmse reaction. Mechanistic studies, including kinetic experiments, were conducted to gain insights into the details of the reaction pathway. The potential synthetic utility of this protocol has also been demonstrated.