Reactivity of methyl mandelate-Ti(IV)-enediolate:: Oxidative homocoupling versus aldol and direct Mannich-type syn-diastereoselective condensation

被引：24

作者：

Clerici, A ^{[1
]}

Pastori, N ^{[1
]}

Porta, O ^{[1
]}

机构：

[1] Politecn Milan, Dipartimento Chim Mat & Ingn Chim Giulio Natta, Sez Chim, I-20131 Milan, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 10期

关键词：

D O I：

10.1021/jo048279f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methyl mandelate undergoes quantitative oxidative homo-coupling on treatment with TiCl4/amine at room temperature. In the presence of ArCHO, quantitative syn-diastereo-selective aldol condensation takes over the dimerization, whereas exclusive Mannich-type syn-diastereo-selective reaction is observed in the presence of both ArCHO and PhNH2. The subsequent reactions of the title intermediate do not depend on how it is generated.

引用

页码：4174 / 4176

页数：3

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