Enantioselective reduction of aromatic ketones with borane catalyzed by (R) -4-thiazolidinecar☐ylic acids or (R) -4-thiazolidine methanol
(R) -4-Thiazolidinecar☐ylic acid. (R) -2. 2-dimethyl-4-thiazolidinecar☐ylic acid. S-ethyl- (L) -cysteine and L-methionine as chiral auxiliaries in the enantioselective catalytic reduction of aromatic ketones with borane have been investigated. When (R) -cyclic sulfur-containing α-amino acids were us...
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| Published in | Tetrahedron: asymmetry Vol. 7; no. 10; pp. 2779 - 2782 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
Elsevier Ltd
01.10.1996
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| Online Access | Get full text |
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| Summary: | (R) -4-Thiazolidinecar☐ylic acid. (R) -2. 2-dimethyl-4-thiazolidinecar☐ylic acid. S-ethyl- (L) -cysteine and L-methionine as chiral auxiliaries in the enantioselective catalytic reduction of aromatic ketones with borane have been investigated. When (R) -cyclic sulfur-containing α-amino acids were used as auxiliaries. the products secondary alcohols possess the (S) -configuration in contrast to Martens' (R) -2-Amino-1. 1-diphenyl-3- (isopropylmercapto) -1-propanol.
On introduction of a sulfur atom, the configuration of chiral alcohols obtained is contrary to that when chiral β-amino alcohols were used as catalyts. [Display omitted] |
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| ISSN: | 0957-4166 1362-511X |
| DOI: | 10.1016/0957-4166(96)00360-6 |