BF3•OEt2-mediated syn-selective Meyer-Schuster rearrangement of phenoxy propargyl alcohols for Z-β-aryl-α,β-unsaturatedesters

被引：10
|
作者：
Puri, Surendra [1 ]
Babu, Madala Hari [1 ]
Reddy, Maddi Sridhar [1 ,2 ]
机构：
[1] CSIR Cent Drug Res Inst, Med & Proc Chem Div, BS 10-1,Sect 10, Lucknow 226031, Uttar Pradesh, India
[2] Acad Sci & Innovat Res, New Delhi 110001, India
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 29期
关键词：
CATALYZED CONVERSION; EFFICIENT SYNTHESIS; CARBONYL-COMPOUNDS; DUAL CATALYSIS; GOLD; CYCLIZATION; ACETATES; KETONES; ALKYNES; ENONES;
D O I：
10.1039/c6ob01090c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Synthesis of Z-beta-aryl-alpha,beta-unsaturated esters from readily available 1-aryl-3-phenoxy propargyl alcohols is achieved via a BF3-mediated syn-selective Meyer-Schuster rearrangement under ambient conditions. The reaction mechanism is postulated to involve an electrophilic borylation of an allene intermediate as the key step to kinetically control the stereoselectivity.
引用
收藏
页码：7001 / 7009
页数：9
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