Halogenated salt assisted Cu-catalyzed asymmetric 1,4-borylstannation of 1,3-enynes: enantioselective synthesis of allenylstannes,Chemical Science

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Halogenated salt assisted Cu-catalyzed asymmetric 1,4-borylstannation of 1,3-enynes: enantioselective synthesis of allenylstannes
Chemical Science ( IF 7.6 ) Pub Date : 2020-12-22 , DOI: 10.1039/d0sc05425a
Jialin Ye ₁ , Yang Liao _{2,

3} , Hao Huang _{2,

3} , Yang Liu _{2,

3} , Dongmei Fang _{2,

3} , Min Wang _{2,

3} , Lianrui Hu ₄ , Jian Liao _{1,

2,

3}

Affiliation

An enantioselective 1,4-borylstannation of 1,3-enynes employed a chiral sulfoxide phosphine (SOP)/Cu complex as a catalyst, and the desired products, chiral allenylstannes, were first synthesized by asymmetric catalysis with satisfactory yields and enantioselectivies. In this protocol, a catalytic amount of additive, a halogenated salt, plays a crucial role in the success. Control experiments and theoretical studies disclosed that the four-membered ring transmetallation transition states which were stabilized by a halide anion are the key to yields and stereochemical outcomes.

中文翻译：

卤化盐辅助铜催化 1,3-烯炔的不对称 1,4-硼基锡化反应：对映选择性合成联二烯基锡

1,3-烯炔的对映选择性1,4-硼基锡化反应采用手性亚砜膦( SOP )/Cu配合物作为催化剂，首先通过不对称催化合成了所需的产物——手性联烯基锡，具有令人满意的产率和对映选择性。在此方案中，催化量的添加剂（卤化盐）在成功中起着至关重要的作用。对照实验和理论研究表明，卤化物阴离子稳定的四元环金属交换过渡态是产率和立体化学结果的关键。

更新日期：2021-01-18

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