手性银配合物催化的 1-吡咯啉-5-羧酸酯对α-烯酮的立体选择性和对映选择性迈克尔加成反应。
Chiral Silver Complex-Catalyzed Diastereoselective and Enantioselective Michael Addition of 1-Pyrroline-5-carboxylates to α-Enones.
机构信息
Department of Applied Chemistry, Institute of Science and Engineering, Chuo University , 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.
出版信息
J Org Chem. 2017 Sep 1;82(17):8927-8932. doi: 10.1021/acs.joc.7b01335. Epub 2017 Aug 21.
A AgOAc/ThioClickFerrophos complex-catalyzed the highly diastereo- and enantioselective reaction between 1-pyrroline-5-carboxylates (1) and acyclic α-enones (2) in MeOH, in the presence of DBU, to give the single isomer Michael adducts (3) in high yields (up to 99%) with excellent enantioselectivies (up to 99% ee). Subsequent reduction of the Michael adducts with sodium cyanoborohydride successfully produced the fused pyrrolizidine ester as an almost pure single stereoisomer.
AgOAc/ThioClickFerrophos 配合物催化 1-吡咯啉-5-羧酸酯（1）和非环 α-烯酮（2）在甲醇中进行高非对映选择性和对映选择性反应，在 DBU 的存在下，以高产率（高达 99%）获得单一异构体迈克尔加成物（3），对映选择性优异（高达 99%ee）。随后用氰基硼氢化钠还原迈克尔加成物，成功地得到了几乎纯的单一立体异构体稠合的吡咯里西啶酯。
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