First anti-Selective Direct Michael Addition of α-Alkoxy Ketones to Enones by Cooperative Catalysis of Samarium(III) Trifluoromethanesulfonate and Tributyltin Methoxide

被引：2

作者：

Esumi, Naoto ^{[1
]}

Nishimoto, Yoshihiro ^{[2
]}

Yasuda, Makoto ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, 2-1 Yamada Oka, Suita, Osaka 5650871, Japan

[2] Osaka Univ, Grad Sch Engn, Frontier Res Base Global Young Researchers Ctr Op, 2-1 Yamada Oka, Suita, Osaka 5650871, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 19期

基金：

日本学术振兴会;

关键词：

Michael addition; Tin; Samarium; Methoxy ketones; Diastereoselectivity; CHIRAL PALLADIUM ENOLATE; LINKED-BINOL COMPLEX; ALPHA; BETA-UNSATURATED KETONES; 1,3-DICARBONYL COMPOUNDS; CONJUGATE ADDITIONS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC CATALYST; ALDOL CYCLIZATION; ESTERS; CONSTRUCTION;

D O I：

10.1002/ejoc.201700501

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new highly anti-diastereoselective Michael addition of alpha-alkoxy ketones to alpha,beta-unsaturated ketones was achieved. This method features a dual-catalyst protocol that combines samarium(III) trifluoromethanesulfonate and Bu3SnOMe. The combination of these two catalysts effectively allowed the generation of enolate species from alpha-alkoxy ketones and produced Michael adducts in high yields with high anti diastereoselectivity. A variety of enones and alpha-alkoxy ketones were applied to this system to give the anti products. One-pot domino Michael/aldol reactions effectively afforded cyclic enones with a defined configuration.

引用

页码：2831 / 2835

页数：5

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