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

doi:10.1055/s-1999-2952

Synlett 1999; 1999(11): 1799-1801
DOI: 10.1055/s-1999-2952

letter

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Abstract

PDF Download All articles of this category

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

PDF (62 kb)