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一种新型手性β-磺酰胺醇/Ti(OiPr)₄/Et₂Zn/R₃N催化剂体系催化的末端炔烃对醛的高度对映选择性加成反应。

Highly enantioselective addition of terminal alkynes to aldehydes catalyzed by a new chiral beta-sulfonamide alcohol/Ti(OiPr)4/Et2Zn/R3N catalyst system.

作者信息

Qiu Li, Wang Quan, Lin Li, Liu Xiaodong, Jiang Xianxing, Zhao Qingyang, Hu Guowen, Wang Rui

机构信息

State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China.

出版信息

Chirality. 2009 Feb;21(2):316-23. doi: 10.1002/chir.20583.

Abstract

A new catalytic system, generated from the readily available and inexpensive beta-sulfonamide alcohol L*, Ti(O(i)Pr)(4), Et(2)Zn, and tertiary amine base (R(3)N), effectively catalyzes the enantioselective addition of various terminal alkynes including some quite challenging alkynes to aldehydes in good yields and excellent enantioselectivities. Up to 96% yield and >99% enantioselectivity were achieved with the use of N,N-diisoproylethylamine (DIPEA) as an additive in this asymmetric addition.

摘要

一种由易于获得且价格低廉的β-磺酰胺醇L*、四异丙氧基钛(Ti(O(i)Pr)(4))、二乙基锌(Et(2)Zn)和叔胺碱(R(3)N)生成的新型催化体系,能够有效地催化各种末端炔烃(包括一些极具挑战性的炔烃)对醛的对映选择性加成反应,反应产率良好,对映选择性优异。在该不对称加成反应中,使用N,N-二异丙基乙胺(DIPEA)作为添加剂时,产率高达96%,对映选择性大于99%。

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