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Synlett 1999; 1999(11): 1799-1801
DOI: 10.1055/s-1999-2952
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A Novel Synthesis of Chiral 1-Allyl-1,2,3,4-tetrahydro-β-carboline Employing Allyltributyltin and Chiral Acyl Chlorides

Takashi Itoh* , Yûji Matsuya, Yasuko Enomoto, Kazuhiro Nagata, Michiko Miyazaki, Akio Ohsawa
  • *School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan; Fax +81-3-37 84-59 82; E-mail: ohsawa@pharm.showa-u.ac.jp
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Publication Date:
31 December 1999 (online)

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β-Carboline was acylated at its 9-position by a chiral acyl chloride, followed by reaction with allyltributyltin and 2,2,2-trichloroethyl chloroformate to afford an 1-allyl-1,2-dihydrocarboline derivative in a diasteroselective manner. The chiral acyl group at N-9 was readily eliminated by aqueous alkali to give carboxylic acid quantitatively without racemization on C-1 position. The formed 1-allyl-1,2-dihydro-β-carboline was transformed to 1-allyl-1,2,3,4-tetrahydro-β-carboline.

β-carboline - allyltributyltin - asymmetric addition - chiral acyl chloride - 2,2,2-trichloroethyl chloroformate