Stereochemistry of c-4-Bromo-r-1-cyano-t-3-methoxy-1, 2, 3, 4-tetrahydroisoquinolines from Isoquinoline Reissert Compounds

Michiharu SUGIURA; Koosuke ASAI; Yoshiki HAMADA; Keiichiro HATANO; Yukihisa KURONO; Hiroko SUEZAWA; Minoru HIROTA

doi:10.1248/cpb.45.928

Michiharu SUGIURA, Koosuke ASAI, Yoshiki HAMADA, Keiichiro HATANO, Yukihisa KURONO, Hiroko SUEZAWA, Minoru HIROTA

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Keywords: Reissert compound, isoquinoline, stereoselective bromine addition, x-ray crystallography, crystal structure, tetrahydroisoquinoline

JOURNAL FREE ACCESS

1997 Volume 45 Issue 5 Pages 928-931

DOI https://doi.org/10.1248/cpb.45.928

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Abstract

Treatment of 2-acyl (or sulfonyl)-1-cyano-1, 2-dihydroisoquinolines with bromine and CH₃OH gave 2-acyl (or sulfonyl)-4-bromo-1-cyano-3-methoxy-1, 2, 3, 4-tetrahydroisoquinolines in a highly stereoselective manner in high yields. The stereochemistry, with 1, 4-cis and 3, 4-trans configurations, was determined by X-ray crystallography.

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