Highly Asymmetric Diels-Alder Cycloaddition of Menthyl (Z)-(S) s-3-(2-Pyridylsulfinyl) propenoate with Cyclohexa-1, 3-diene

YOSHITSUGU ARAI; MASANORI TAKADOI; TORU KOIZUMI

doi:10.1248/cpb.36.4162

Highly Asymmetric Diels-Alder Cycloaddition of Menthyl (Z)-(S) _s-3-(2-Pyridylsulfinyl) propenoate with Cyclohexa-1, 3-diene

YOSHITSUGU ARAI, MASANORI TAKADOI, TORU KOIZUMI

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Keywords: Diels-Alder reaction, high diastereoselectivity, menthyl (Z)-(S) _s-3-(2-pyridylsulfinyl) propenoate, chiral sulfoxide, cyclohexa-1, 3-diene, bicyclo [2.2.2] oct-5-ene

JOURNAL FREE ACCESS

1988 Volume 36 Issue 10 Pages 4162-4166

DOI https://doi.org/10.1248/cpb.36.4162

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Abstract

The Diels-Alder reaction of menthyl (Z)-(S) _s-3-(2-pyridylsulfinyl) propenoate with cyclohexa-1, 3-diene in the presence of a Lewis acid, zinc bromide, afforded the endo cycloadduct in a highly diastereoselective manner in excellent yield. The absolute stereochemistry of the adduct was determined by transformation into (+)-bicyclo [2.2.2] oct-5-ene-2-endo-methanol with known absolute configuration.

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