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A Convergent General Strategy for the Functionalized 2‐Aryl Cycloalkyl‐Fused Chromans: Intramolecular Hetero‐Diels–Alder Reactions of ortho ‐Quinone Methides
Author(s) -
Tummatorn Jumreang,
Ruchirawat Somsak,
Ploypradith Poonsakdi
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200902403
Subject(s) - intramolecular force , chemistry , quinone , aryl , diels–alder reaction , quinone methide , organic chemistry , medicinal chemistry , catalysis , alkyl
Five and six : 3,4‐Cyclopentyl‐ and cyclohexyl‐fused 2‐arylchromans could be readily prepared from the intramolecular hetero‐Diels–Alder reactions of the corresponding ortho ‐quinone methide ( o ‐QM) precursors tethered to the styrenes under mild reaction conditions. The products were obtained with good to excellent diastereoselectivity (up to>99:1 dr; see scheme; MOM=methoxymethyl).