Chirale Synthesebausteine aus Aminosäuren: Dihydrothiazol-Derivate (Δ4-Thiazoline) aus Cystein
Reaction of cysteine with pivalaldehyde and protection at the nitrogen atom with benzyl chloroformate give the diastereomerically pure cyclic N,S-acetal 2 which is selectively oxidized to the sulfoxide 3. Thiazoline 5 is obtained after oxidative, electrochemically induced decarboxylation and subseq...
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| Main Authors: | , , , |
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| Format: | Article |
| Language: | deu |
| Published: |
Swiss Chemical Society
1989-10-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9925 |
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| Summary: | Reaction of cysteine with pivalaldehyde and protection at the nitrogen atom with benzyl chloroformate give the diastereomerically pure cyclic N,S-acetal 2 which is selectively oxidized to the sulfoxide 3. Thiazoline 5 is obtained after oxidative, electrochemically induced decarboxylation and subsequent elimination of acetic acid. The oxidation level of the sulfur can be varied (sulfide 6 and sulfone 7). The carboxylated thiazoline 9 is obtained in three steps from 3 via esterification, Pummerer rearrangement, and elimination of the silyloxy intermediate. – These dihydrothiazole heterocycles with one or two stereogenic centres offer a new perspective to the use of cysteine as a chiral building block.
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| ISSN: | 0009-4293 2673-2424 |