Stereoselectivity, regioselectivity and mechanism in the intramolecular 'citran' bicyclisation of chromenes

被引：6
作者：
Calderon-Higginson, C [1 ]
Crombie, L [1 ]
Redshaw, SD [1 ]
Whiting, DA [1 ]
机构：
[1] Univ Nottingham, Dept Chem, Nottingham NG7 2RD, England
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 15期
关键词：
D O I：
10.1039/b001310m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Stereochemical evidence suggests that acid catalysed citran formation proceeds via electrocyclisation of a dienone, and that pyrolysis of 'farnesylidenemalonic acid' proceeds with retention of configuration at the newly formed 8-olefin bond, indicating the operation of forward and reverse Diels-Alder processes respectively; 1,3-dihydroxynaphthalene reacts with citral in pyridine to yield chromene and citran products in a regioselective fashion.
引用
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页码：2491 / 2494
页数：4
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