Super Acid-Induced Pummerer-Type Cyclization Reaction : Improvement in the Synthesis of Chiral 1,3-Dimethyl-1,2,3,4-tetrahydroisoquinolines

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概要

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• Improved synthesis of four stereoisomeric chiral l,3-dimethyl-1,2,3,4-tetrahydroisoquinolines (1a, b, ent-1a, b) was achieved via the super acid-induced cyclization of chiral N-[1-methyl-2-(phenylsulfiyr)ethyl]-N-(1-phenylethyl)formamides (4a,b, ent-4a,b) using the Pummerer-type cyclization reaction as a key step. The cyclization leading to the isoquinoline ring proceeded in a quantitative manner when trifluoromethane sulfonicacid (TFSA) was used as the super acid, although Friedel-Crafts-type alkylation of 4-phenyisulfanyl TIQ derivatives (5) with benzene used as the solvent accompanied cyclization to yield the 4-phenyl-TIQs (7). The byproduct (7) was exclusively formed when a large excess amount of TFSA was used.

• 公益社団法人日本薬学会の論文
• 2003-06-01

著者

• 佐野 武弘

  昭和薬科大学

• 佐野 武弘

  Showa Pharmaceutical Univ. Tokyo Jpn

• SANO Takehiro

  Showa College of Pharmaceutical Sciences

• SAITOH Toshiaki

  Showa College of Pharmaceutical Sciences

• HORIGUCHI Yoshie

  Showa College of Pharmaceutical Sciences

• SHIKIYA Kentaro

  Showa Pharmaceutical University

• Horiguchi Y

  Showa Pharmaceutical University

• Sakurai K

  Showa Pharmaceutical University

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