Enantioselective Carbon-Carbon Bond Formation by Chiral Organotitanium Compounds; Methyltitanium (S) -N-Acylpyrrolidinylmethoxide Diisopropoxides

HIROSHI TAKAHASHI; AKIHIRO KAWABATA; KIMIO HIGASHIYAMA

doi:10.1248/cpb.35.1604

HIROSHI TAKAHASHI, AKIHIRO KAWABATA, KIMIO HIGASHIYAMA

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Keywords: (S) -N-acylpyrrolidinylmethanol, carbon-carbon bond formation, enantioselective reaction, methyltitanium diisopropoxide, (R) -1- (1-naphthyl) ethanol, (R) -1-phenylethanol, (5) -prolinol

JOURNAL FREE ACCESS

1987 Volume 35 Issue 4 Pages 1604-1607

DOI https://doi.org/10.1248/cpb.35.1604

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Abstract

New chiral compounds, (S) -N-acylpyrrolidinylmethanols (1b-f and 1h), were synthesized and chiral methyltitanium diisopropoxides (2a-h) were prepared from 1a-h. Enantioselective carbon-carbon bond formation between aromatic carbaldehydes and 2a-h was achieved in yields of 90-97% and 10.5-54.1%ee. The chiral auxiliaries (1a-h) were recovered in almost quantitative yields without any loss of optical purity.

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