A Convergent General Strategy for the Functionalized 2‐Aryl Cycloalkyl‐Fused Chromans: Intramolecular Hetero‐Diels–Alder Reactions of  ortho ‐Quinone Methides | Zendy

Tummatorn Jumreang | Zendy; Ruchirawat Somsak | Zendy; Ploypradith Poonsakdi | Zendy

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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).

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