A stereoselective synthesis of anti-γ,δ-alkynyl- and -alkenyl-β-hydroxy-α-amino esters from tin(II) enolates of glycinate

被引：14

作者：

Gridley, JJ ^{[1
]}

Coogan, MP ^{[1
]}

Knight, DW ^{[1
]}

Malik, KMA ^{[1
]}

Sharland, CM ^{[1
]}

Singkhonrat, J ^{[1
]}

Williams, S ^{[1
]}

机构：

[1] Cardiff Univ, Dept Chem, Cardiff CF10 3TB, S Glam, Wales

来源：

CHEMICAL COMMUNICATIONS | 2003年 / 20期

关键词：

D O I：

10.1039/b306291k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Condensations between the tin(II) enolate 11 of ethyl N-tosylglycinate and conjugated ynals 12 and ynones 14 are highly diastereoselective, in favour of the anti-isomers 13 and 15; similar reactions of enals and enones 17 show lower but still useful levels of anti-stereoselectivity.

引用

页码：2550 / 2551

页数：2

共 14 条

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Knight, DW ;

Redfern, AL ;

Gilmore, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (05) :622-628

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Knight, DW ;

Redfern, AL ;

Gilmore, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (21) :2874-2883

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Soloshonok, VA .

CURRENT ORGANIC CHEMISTRY, 2002, 6 (04) :341-364

[14] α-imino esters:: Versatile substrates for the catalytic, asymmetric synthesis of α- and β-amino acids and β-lactams [J].

Taggi, AE ;

Hafez, AM ;

Lectka, T .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (01) :10-19

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