Synthesis of α-Functionalized Trichloromethylcarbinols

被引：15

作者：

Ram, Ram N. ^{[1
]}

Soni, Vineet Kumar ^{[1
]}

机构：

[1] Indian Inst Technol Delhi, Dept Chem, New Delhi 110016, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 17期

关键词：

ONE-POT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; AMINO-ACIDS; CYCLOADDITION REACTIONS; PRACTICAL SYNTHESIS; CARBONYL-COMPOUNDS; ALDEHYDES; KETONES; TRIMETHYL(TRICHLOROMETHYL)SILANE;

D O I：

10.1021/acs.joc.5b01547

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new series of alpha-functionalized trichloromethylcarbinols have been synthesized from corresponding alpha-halomethyl ketones, esters, and amides in 48-78% overall yields. Reactivity of nitrates obtained in the first step was dependent on the electron-withdrawing nature of the functional groups, and increases with increasing electron deficiency. Synthetic applications of such trichloromethylcarbinols for the preparation of chloromethyl-alpha-diketones, trichloromethylated dihydrofurans, and enol acetates of alpha-functionalized acid chlorides have been demonstrated. The reaction of these compounds in the Jocic-Reeve reaction was also demonstrated.

引用

页码：8922 / 8928

页数：7

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