alpha,alpha'-dioxothiones .2. Asymmetric Diels-Alder reactions of chiral non-racemic alpha,alpha'-dioxothiones

被引：13

作者：

Boccardo, G ^{[1
]}

Capozzi, G ^{[1
]}

Giuntini, M ^{[1
]}

Menichetti, S ^{[1
]}

Nativi, C ^{[1
]}

机构：

[1] UNIV FLORENCE,DIPARTIMENTO CHIM ORGAN,CNR,CTR CHIM COMPOST ETEROCICLICI,I-50121 FLORENCE,ITALY

来源：

TETRAHEDRON | 1997年 / 53卷 / 51期

关键词：

D O I：

10.1016/S0040-4020(97)10162-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral non-racemic alpha,alpha'-dioxothiones 2a-g and 17 are obtained from chiral beta-ketoesters using the phthalimidesulfenyl chloride 1 as key reagent. The ability of these thiones to discriminate between the enantiotopic faces of several dienophiles has been evaluated, The best diastereoisomeric excesses (67-80%) were obtained when the alpha-acyl thiones were involved as electron-poor dienes in inverse electron demand Diels-Alder reactions with electron-rich styrenes as dienophiles. The possibility to obtain thiones bearing two,chiral groups as-well as the reactions where the alpha-acyl thiones 2 participate as dienophiles are also shown. (C) 1997 Elsevier Science Ltd.

引用

页码：17383 / 17394

页数：12

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