Enantiopure 2-sulfinylbuta-1,3-dienes in Diels-Alder cycloadditions: a stereoselective approach to an azasteroidal skeleton

被引：23

作者：

Aversa, MC

Barattucci, A

Bonaccorsi, P

Bruno, G

Caruso, F

Giannetto, P

机构：

[1] Univ Messina, Dipartimento Chim Organ & Biol, I-98166 Messina, Italy

[2] Univ Messina, Dipartimento Chim Inorgan Chim Analit & Chim Mat, I-98166 Messina, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 20期

关键词：

D O I：

10.1016/S0957-4166(01)00507-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of enantiopure 4-[1-(alkylsulfinyl)vinyl]-1,2-dihydronaphthalenes and their Diels-Alder reactions are described. Cycloadditions with N-phenylmaleimide occur under thermal conditions, very slowly but with notable stereoselection, giving in each case just one of the two endo adducts in high yield. The obtained 16-azasteroid derivatives undergo chiral auxiliary removal in the presence of TMSI. (C) 2001 Published by Elsevier Science Ltd.

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页码：2901 / 2908

页数：8

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