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Pt(IV)-catalyzed generation and [4+2]-cycloaddition reactions of o-quinone methides

Author:
Radomkit, Suttipol, Sarnpitak, Pakornwit, Tummatorn, Jumreang, Batsomboon, Paratchata, Ruchirawat, Somsak, Ploypradith, Poonsakdi
Source:
Tetrahedron 2011 v.67 no.21 pp. 3904-3914
ISSN:
0040-4020
Subject:
alkenes, chemical reactions, chemical structure
Abstract:
Novel intermolecular and intramolecular generations of ortho-quinone methides and their formal [4+2]-cycloaddition reactions with olefins catalyzed by PtCl₄ and AuCl₃ under mild conditions have been developed. Good to excellent yields (up to 99%) and diastereoselectivity (up to >99:1) of the chromans were obtained. PtCl₄ was found to be effective and compatible with various functional groups present in the substrates. A mechanism accounting for its catalytic cycle is proposed and discussed.
Agid:
1093736