Unravelling the Nucleophilicity of Buten tides for 1,6-Conjugate Addition to p-Quinone Methides: A Direct Access to Diversely Substituted Butenolide-Derived Diarylmethanes

被引：36

作者：

Sharma, Brijesh M. ^{[1
,2
]}

Shinde, Dinesh R. ^{[3
]}

Jain, Ruchi ^{[1
,2
]}

Begari, Eeshwaraiah ^{[1
,2
]}

Satbhaiya, Shruti ^{[1
,2
]}

Gonnade, Rajesh G. ^{[4
]}

Kumar, Pradeep ^{[1
,2
]}

机构：

[1] Natl Chem Lab, Div Organ Chem, CSIR, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

[2] Acad Sci & Innovat Res AcSIR, New Delhi 110025, India

[3] Natl Chem Lab, CSIR, Cent NMR Facil, Pune 411008, Maharashtra, India

[4] Natl Chem Lab, CSIR, Phys & Mat Chem Div, Pune 411008, Maharashtra, India

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 09期

关键词：

MICHAEL REACTION; ENANTIOSELECTIVE SYNTHESIS; GAMMA-BUTYROLACTONES; CHEMISTRY; MUKAIYAMA; ALDOL; TRIARYLMETHANES; SECOLIGNANS; DERIVATIVES; ALLYLATION;

D O I：

10.1021/acs.orglett.8b00745

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Lewis acid catalyzed regioselective C-C bond is constructed through beta-addition of deconjugated butenolides with p-quinone methides in a 1,6-conjugate addition manner. Interestingly, Lewis acid catalyzed vinylogous Mukaiyama-Michael reaction of silyloxyfurans with p-QMs proceeds selectively through the alpha or gamma position exclusively. The reaction is mild with broad substrate scope, thus allowing easy access to a wide range of bis-arylated alpha-/beta-/gamma-substituted butenolides.

引用

页码：2787 / 2791

页数：5

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