Chiral Silver Alkoxide Catalyzed Asymmetric Aldol Reaction of Alkenyl Esters with Isatins

Chiral Silver Alkoxide Catalyzed Asymmetric Aldol Reaction of Alkenyl Esters with Isatins
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手性醇银催化烯基酯与靛红的不对称羟醛反应

DOI:
10.1055/a-1479-4694
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发表时间:
2021
期刊:
影响因子:
2
通讯作者:
A. Yanagisawa and A. Kawada
A. Yanagisawa and A. Kawada
中科院分区:
化学4区
文献类型:
--
作者:
Tanaka Susumu;Konishi Masafumi;Imoto Hiroaki;Nakamura Yuma;Ishida Masatoshi;Furuta Hiroyuki;Naka Kensuke;川幡正俊,富永昌英,小松亮太,兵頭直,山口健太郎;A. Yanagisawa and A. Kawada

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以DM-BINAP·AgOTf为手性预催化剂,N,N-二异丙基乙胺为碱催化剂,在甲醇或2,2,2-三氟乙醇存在下,实现了烯基酯与靛红的不对称羟醛缩合反应.光学活性的3-烷基化3-羟基-2-羟吲哚具有高达98%ee的非对映选择性地获得中到高产率,不仅从环状烯基酯,而且从无环的通过原位生成的手性银烯醇化物。
A catalytic enantioselective aldol reaction of alkenyl esters with isatins was achieved using a DM-BINAP·AgOTf complex as the chiral precatalyst andN,N-diisopropylethylamine as the base precatalyst in the presence of methanol or 2,2,2-trifluoroethanol. Optically active 3-alkylated 3-hydroxy-2-oxindoles having up to 98% ee were diastereoselectively obtained in moderate to high yields not only from cyclic alkenyl esters but also from acyclic ones through the in situ generated chiral silver enolates.
DOI: 10.1016/s0040-4020(01)82741-1
发表时间: 1969
期刊: Tetrahedron
影响因子: 2.1
作者:
J. Libman;M. Sprechert;Y. Mazur
通讯作者: Y. Mazur