Enantioselective Radical Alkynylation of C(sp3)-H Bonds Using Sulfoximine as a Traceless Chiral Auxiliary
Enantioselective Radical Alkynylation of C(sp3)-H Bonds Using Sulfoximine as a Traceless Chiral Auxiliary
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DOI：
10.1002/asia.201402983
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发表时间：
2015-01-01
影响因子：
4.1
通讯作者：
Inoue, Masayuki
中科院分区：
文献类型：
--
作者：
Nagatomo, Masanori;Yoshioka, Shun;Inoue, Masayuki
在光照射条件下，仅用手性对甲苯基叔丁基二甲基硅基乙炔基亚砜亚胺和二苯甲酮实现了邻氮原子C（sp（3））H键的不对称炔基化反应.一个二碳炔单元被化学和对映选择性地转移到氮取代的亚甲基上，以产生各种结构的光学活性炔丙胺。值得注意的是，NH-未保护的亚砜亚胺基团有效地将其立体化学信息传递给产物，并作为无痕手性助剂发挥作用。
Enantioselective alkynylation of C(sp(3))H bonds adjacent to a nitrogen atom has been achieved using only chiral p-tolyl tert-butyldimethylsilylethynyl sulfoximine and benzophenone under photo-irradiation conditions. A two-carbon alkyne unit was chemo- and enantioselectively transferred at the nitrogen-substituted methylene to produce the optically active propargylic amines of various structures. Remarkably, the NH-unprotected sulfoximine group efficiently transmits its stereochemical information to the product and functions as a traceless chiral auxiliary.