Enantioselective Iodine(III)-Mediated Synthesis of α-Tosyloxy Ketones: Breaking the Selectivity Barrier

被引：56

作者：

Basdevant, Benoit ^{[1
]}

Legault, Claude Y. ^{[1
]}

机构：

[1] Univ Sherbrooke, Dept Chem, Ctr Green Chem & Catalysis, Sherbrooke, PQ J1K 2R1, Canada

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 19期

基金：

加拿大创新基金会; 加拿大自然科学与工程研究理事会;

关键词：

HYDROXYLATIVE PHENOL DEAROMATIZATION; HYPERVALENT IODINE; ASYMMETRIC-SYNTHESIS; CARBOXYLIC-ACIDS; OXIDATION; SPIROLACTONIZATION; CATALYSIS; FUNCTIONALIZATIONS; IODOARENES; COMPLEXES;

D O I：

10.1021/acs.orglett.5b02501

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The development of practical methods to access chiral nonracemic alpha-substituted ketones is of particular importance due to their ubiquitous nature. Unprecedented levels of enantioselectivity are reported for the synthesis of alpha-tosyloxy ketones, using enol esters and chiral iodine(III) reagents. The reaction can be performed under both stoichiometric and catalytic conditions. These results suggest widely different reaction mechanisms for the reaction of ketones versus enol esters, supporting recent computational insights.

引用

页码：4918 / 4921

页数：4

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