Double conjugate addition of dithiols to propargylic carbonyl systems to generate protected 1,3-dicarbonyl compounds

被引：32

作者：

Sneddon, HF ^{[1
]}

van den Heuvel, A ^{[1
]}

Hirsch, AKH ^{[1
]}

Booth, RA ^{[1
]}

Shaw, DM ^{[1
]}

Gaunt, MJ ^{[1
]}

Ley, SV ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 07期

关键词：

D O I：

10.1021/jo052514s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The work describes the efficient double conjugate addition of ethane and propane dithiols in the presence of sodium methoxide to a wide variety of propargylic carbonyl containing compounds. The products of these reactions are differentiated, 1,3-dicarbonyl systems useful for various synthesis programs. By judicious use of hydroxylated substrates tandem cyclization occurs to afford tetrahydropyran lactols or, in the case of hydroxy-substituted propargylic esters, lactones. The corresponding amino-substituted propargylic aldehydes gives piperidine derivatives upon double conjugate addition tandem cyclization.

引用

页码：2715 / 2725

页数：11

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