First hetero-Diels-Alder reaction of an enantiopure 2-sulfinylbuta-1,3-diene: mild and effective stereocontrolled synthesis of pyranoid derivatives

被引：20

作者：

Aversa, MC ^{[1
]}

Barattucci, A ^{[1
]}

Bonaccorsi, P ^{[1
]}

Bruno, G ^{[1
]}

Giannetto, P ^{[1
]}

Panzalorto, M ^{[1
]}

机构：

[1] UNIV MESSINA,DIPARTIMENTO CHIM INORGAN CHIM ANALIT & CHIM FIS,I-98166 MESSINA,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 17期

关键词：

D O I：

10.1016/S0957-4166(97)00345-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

LiClO4 catalyzed cycloaddition of (R-s,E)-3-[(1S)-isoborneol-10-sulfinyl]-1-methoxybuta-1,3-diene 1 with ethyl glyoxalate occurred with good endo and facial diastereoselectivities to give (2R,6S,R-S)-6-ethoxycarbonyl-4-[(1S)-isoborneol-10-sulfinyl]-2-methoxy-5,6-dihydro-2H-pyran 2 as the main product, easily isolated as crystalline material in high yield. (C) 1997 Elsevier Science Ltd.

引用

页码：2989 / 2995

页数：7

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