Catalytic Conjugate Addition of Acyl Anion Equivalents Promoted by Fluorodesilylation
Catalytic Conjugate Addition of Acyl Anion Equivalents Promoted by Fluorodesilylation
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DOI：
10.1021/ol403041k
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发表时间：
2014-01-03
期刊：
影响因子：
5.2
通讯作者：
Cullen, Lindsey R.
中科院分区：
文献类型：
--
作者：
Denmark, Scott E.;Cullen, Lindsey R.
使用亚化学计量的 TBAF 实现了源自 2-甲硅烷基-1,3-二噻烷的酰基阴离子等价物与 α,β-不饱和酮和酯的共轭加成。将芳基-1,3-二噻烷加成到各种环状和无环α,β-不饱和羰基受体上时观察到高产率和短反应时间。还介绍了通过 C-13 NMR 光谱观察反应性阴离子以及扩展到不对称变体。
The conjugate addition of acyl anion equivalents derived from 2-silyl-1,3-dithianes to alpha,beta-unsaturated ketones and esters has been achieved using a substoichiometric amount of TBAF. High yields and short reaction times are observed for the addition of aryl-1,3-dithianes to a variety of cyclic and acyclic alpha,beta-unsaturated carbonyl acceptors. Observation of the reactive anion by C-13 NMR spectroscopy and extension to an-asymmetric variant is also presented.