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Intramolecular Diels−Alder Reaction of Chiral Silatrienes: Synthesis of 4a,7,8,8a‐Tetrahydro‐4‐silaisochroman‐1‐ones
Author(s) -
Coelho Paulo J.,
Blanco Luis
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200009)2000:17<3039::aid-ejoc3039>3.0.co;2-x
Subject(s) - intramolecular force , chemistry , diels–alder reaction , methyl acrylate , acrylate , catalysis , intramolecular reaction , silicon , medicinal chemistry , organic chemistry , stereochemistry , monomer , copolymer , polymer
Intramolecular Diels−Alder reactions of chiral 2‐silahexa‐3,5‐dienyl α,β‐unsaturated esters have been found to afford tetrahydro‐4‐silaisochroman‐1‐ones in moderate yields. The best diastereoselectivity was achieved in the reaction of silatriene 8c , in which methyl and triisopropylsilyloxymethyl groups are attached to the silicon atom, with an acrylate as the dienophile under EtAlCl 2 ‐catalyzed conditions.