Stereocontrolled Generation of α-Metalated S,O-Acetals by Sulfoxide-Ligand Exchange from Cyclic Dithioorthoformate Monooxides

被引：12

作者：

Barsamian, Adam L. ^{[1
]}

Blakemore, Paul R. ^{[1
]}

机构：

[1] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA

来源：

ORGANOMETALLICS | 2012年 / 31卷 / 01期

基金：

美国国家科学基金会;

关键词：

CHIRAL ORGANOMETALLIC REAGENTS; BORONIC ESTERS; LITHIATION-SUBSTITUTION; REACTION PATHWAYS; HOMOLOGATION; CARBANIONS; SULFUR; REARRANGEMENT; CARBENOIDS; BORANES;

D O I：

10.1021/om200858v

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Treatment of trans or cis 2-isopentoxy-1,3-benzodithiolane-S-oxides with EtMgCl gave configurationally stable (>= 2.5 h, at -78 degrees C) stereodefined alpha-magnesiated S,O-acetals that incorporated D atoms in a stereospecific manner upon reaction with CD3OD. alpha-Lithiated S,O-acetals generated in the same fashion using PhLi were found to be less configurationally stable.

引用

页码：19 / 22

页数：4

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