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Communication | Special issue | Vol 47, No. 1, 1998, pp.65-68
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)3
Optical Resolution and Asymmetric Synthesis of Benzyl 3,5-Dimethyl-4-(2,2,2-trifluoro-1-hydroxyethyl)pyrrole-2-carboxylate

Masaaki Omote, Akira Ando, Toshiyuki Takagi, Mayumi Koyama, Itsumaro Kumadaki,* and Motoo Shiro

*Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata-shi, Osaka 573-0101, Japan

Abstract

For the total synthesis of 3- and 8-(2,2,2-trifluoro-1-hydroxyethyl)deuteroporphyrin dimethyl esters (2, and 3) in a large scale by ring closure, the camphanyl ester (5) of the titled ester (4) was resolved, but hydrolysis of the resolved 5 was unsuccessful. Oxidation of 4 with Dess-Martin reagent gave 3-trifluoromethylcarbonyl compound (6), which was reduced with catecholborane in the presence of a chiral catalyst to a chiral isomer of 4 in a high enantiomeric excess.