STEREOSELECTIVITY IN THE SYNTHESIS OF POLYACENE DERIVATIVES BY REPETITIVE DIELS-ALDER REACTIONS

被引：8

作者：

ASHTON, PR

BROWN, GR

SMITH, DR

STODDART, JF

WILLIAMS, DJ

机构：

[1] UNIV BIRMINGHAM,SCH CHEM,BIRMINGHAM B15 2TT,W MIDLANDS,ENGLAND

[2] ZENECA PHARMACEUT,MACCLESFIELD SK10 4TG,CHESHIRE,ENGLAND

[3] UNIV SHEFFIELD,DEPT CHEM,SHEFFIELD S3 7HF,S YORKSHIRE,ENGLAND

[4] IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM,LONDON SW7 2AY,ENGLAND

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 51期

关键词：

D O I：

10.1016/S0040-4039(00)61425-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The bisaryne generated from 1,4,5,8-tetramethyl-2,3,6,7-tetrabromonaphthalene reacts with 2,5-dimethylfuran to give - through the intermediacy of the 1:1 adduct 1 - the 2:1 adducts 2, with the major isomer 2a, the one with the anti-configuration as revealed by X-ray crystallography and rationalised by molecular mechanics. Diels-Alder reactions of the anti-bisdienophile 2a with 2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1]heptane proceed with complete treble diastereoselectivity to give only one 1:1 adduct 3 and a single 2:1 adduct 4.

引用

页码：8337 / 8340

页数：4

共 25 条

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