Vinylogous Aldol Reaction of a Silyloxydiene Promoted by Sulfoxides, as Lewis Bases: 1,4-asymmetric Induction Mediated by a Remote Methylsulfinyl Group

被引：4
作者：
Acocella, Maria Rosaria [1 ]
Villano, Rosaria [2 ]
Costabile, Chiara [1 ]
Scettri, Arrigo [1 ]
机构：
[1] Univ Salerno, Dipartimento Chim & Biol, I-84084 Salerno, Italy
[2] Ist Chim Biomol CNR, I-07040 Sassari, Italy
来源：
CURRENT ORGANIC CHEMISTRY | 2013年 / 17卷 / 08期
关键词：
Vinylogous; sulfoxide; Lewis Bases; asymmetric-induction; silyloxydiene; NON-RACEMIC 6-(FURAN-3-YL)-5,6-DIHYDRO-PYRAN-2-ONES; SOLVENT-FREE MUKAIYAMA; ASYMMETRIC ALLYLATION; CHIRAL SULFOXIDES; ENANTIOSELECTIVE SYNTHESIS; ACETOACETIC ESTERS; NATURAL-PRODUCTS; SULFINYL GROUP; ALDEHYDES; CONDENSATION;
D O I：
10.2174/1385272811317080013
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A versatile procedure for the gamma-vinylogous aldol reaction of the dioxinone-derived silyl enolether, via enolate activation with an appropriate neutral Lewis base, was formulated. High levels of diastereo- and enantioselectivity using chiral 2-methylsulfinyl benzaldehyde were obtained, pointing out the dual role of the methylsulfinyl group as incorporated chiral inductor and activator of the silyloxydiene in the stereoselective vinylogous aldol reaction.
引用
收藏
页码：886 / 890
页数：5
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