Catalytic Asymmetric Conjugate Addition of a Borylalkyl Copper Complex for Chiral Organoboronate Synthesis
Catalytic Asymmetric Conjugate Addition of a Borylalkyl Copper Complex for Chiral Organoboronate Synthesis
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DOI：
10.1002/anie.201909712
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发表时间：
2019-10-22
影响因子：
16.6
通讯作者：
Yun, Jaesook
中科院分区：
文献类型：
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作者：
Jang, Won Jun;Yun, Jaesook
我们报道了由1,1-二硼基甲烷衍生物原位生成的硼基烷基铜亲核试剂催化对映选择性加成到α， β不饱和二酯。在手性n -杂环碳(NHC)-铜催化剂的存在下，该方法促进了CH(2)Bpin片段在二酯的β位置的对映选择性结合，收率高达86%，具有很高的对映选择性。手性二酯产物中的烷基硼部分通过C-B键的有机转化转化为各种官能团。
We report the catalytic enantioselective conjugate addition of a borylalkyl copper nucleophile generated in situ from a 1,1-diborylmethane derivative to alpha,beta-unsaturated diesters. In the presence of a chiral N-heterocyclic carbene (NHC)-copper catalyst, this method facilitated the enantioselective incorporation of a CH(2)Bpin moiety at the beta-position of the diesters to yield beta-chiral alkyl boronates in up to 86% yield with high enantioselectivity. The alkylboron moiety in the resulting chiral diester products was converted into various functional groups by organic transformation of the C-B bond.