Synthesis and Diels-Alder reactions of N-(tert-butoxycarbonyl)-3-p-tolylsulfinyl-1-benzoquinone-4-imine

被引：6

作者：

Bartolome, JM ^{[1
]}

Carreno, MC ^{[1
]}

Urbano, A ^{[1
]}

机构：

[1] UNIV AUTONOMA MADRID,DEPT QUIM ORGAN CI,E-28049 MADRID,SPAIN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 18期

关键词：

D O I：

10.1016/0040-4039(96)00491-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compound was synthesized in 3 steps (regioselective sulfenylation, m-CPBA and Pb(OAc)(4) oxidations) from N-Boc-p-anisidine. Its Diels-Alder reactions with cyclopentadiene took place on the double bonds C-2-C-3 or C-5-C-6 depending upon the experimental conditions with total endo-selectivity and high pi-facial diastereoselectivity. The cycloaddition with trans-piperylene ocurred exclusively on the sulfinylsubstituted dienophilic double bond C-2-C-3. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：3187 / 3190

页数：4

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