Two-Component Assembly of Thiochroman-4-ones and Tetrahydrothiopyran-4-ones Using a Rhodium-Catalyzed Alkyne Hydroacylation/Thio-Conjugate-Addition Sequence

被引：26

作者：

Bouisseau, Anais ^{[1
]}

Glancy, John ^{[1
]}

Willis, Michael C. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Mansfield Rd, Oxford OX1 3TA, England

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 21期

基金：

英国工程与自然科学研究理事会;

关键词：

DIRECT INTERMOLECULAR HYDROACYLATION; FORMING TRANSFER HYDROGENATION; ALDEHYDE OXIDATION LEVEL; S-SUBSTITUTED ALDEHYDES; ARYL METHYL SULFIDES; BETA; GAMMA-UNSATURATED KETONES; SELECTIVE HYDROACYLATION; AROMATIC-ALDEHYDES; ALKENES; BOND;

D O I：

10.1021/acs.orglett.6b02909

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta'-Thio-substituted-enones, assembled from the combination of beta-tert-butylthio-substituted aldehydes and alkynes, using rhodium catalysis, are shown to smoothly undergo in situ intramolecular S-conjugate addition to deliver a range of S-heterocycles in a one-pot process. Aryl, alkenyl, and alkyl aldehydes can all be employed, to provide thiochroman-4-ones, hexahydro-4H-thiochromen-4-ones, and tetrahydrothiopyran-4-ones, respectively. A variety of in situ oxidations are also performed, allowing access to S,S-dioxide derivatives, as well as unsaturated variants.

引用

页码：5676 / 5679

页数：4

共 68 条

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