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Intramolecular Substitution Reaction of Alkylidene‐Lithium Carbenoids: Regioselective Synthesis of Indenes
Author(s) -
Yanagisawa Hideyuki,
Miura Kasei,
Kitamura Mitsuru,
Narasaka Koichi,
Ando Kaori
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200210)85:10<3130::aid-hlca3130>3.0.co;2-e
Subject(s) - regioselectivity , chemistry , geminal , dihydropyran , intramolecular force , lithium (medication) , moiety , nucleophilic substitution , nucleophile , substitution reaction , medicinal chemistry , indene , organic chemistry , stereochemistry , catalysis , medicine , endocrinology
Intramolecular substitution reaction of geminal dibromo alkenes proceeds to afford indenes, dihydronaphthalenes, dihydrofurans, and dihydropyran via in situ generated lithium alkylidene carbenoids, which have a carbon or oxygen nucleophilic moiety. This reaction provides a regioselective method for the preparation of polysubstituted indenes.