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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| Format: | Article |
| Language: | deu |
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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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| _version_ | 1850283642109034496 |
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| author | Dieter Seebach André Jeanguenat Jürgen Schmidt Thomas Maetzke |
| author_facet | Dieter Seebach André Jeanguenat Jürgen Schmidt Thomas Maetzke |
| author_sort | Dieter Seebach |
| collection | DOAJ |
| description |
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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| format | Article |
| id | doaj-art-5999fd21d4e44acaa341b3e111a3a1cc |
| institution | OA Journals |
| issn | 0009-4293 2673-2424 |
| language | deu |
| publishDate | 1989-10-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj-art-5999fd21d4e44acaa341b3e111a3a1cc2025-08-20T01:47:44ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24241989-10-01431010.2533/chimia.1989.314Chirale Synthesebausteine aus Aminosäuren: Dihydrothiazol-Derivate (Δ4-Thiazoline) aus CysteinDieter Seebach0André Jeanguenat1Jürgen Schmidt2Thomas Maetzke3Laboratorium für Organische Chemie Eidgenössische Technische Hochschule Zürich ETH-Zentrum, Universitätstrasse 16 CH-8092 ZürichLaboratorium für Organische Chemie Eidgenössische Technische Hochschule Zürich ETH-Zentrum, Universitätstrasse 16 CH-8092 ZürichLaboratorium für Organische Chemie Eidgenössische Technische Hochschule Zürich ETH-Zentrum, Universitätstrasse 16 CH-8092 ZürichLaboratorium für Organische Chemie Eidgenössische Technische Hochschule Zürich ETH-Zentrum, Universitätstrasse 16 CH-8092 Zürich 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. https://www.chimia.ch/chimia/article/view/9925 |
| spellingShingle | Dieter Seebach André Jeanguenat Jürgen Schmidt Thomas Maetzke Chirale Synthesebausteine aus Aminosäuren: Dihydrothiazol-Derivate (Δ4-Thiazoline) aus Cystein CHIMIA |
| title | Chirale Synthesebausteine aus Aminosäuren: Dihydrothiazol-Derivate (Δ4-Thiazoline) aus Cystein |
| title_full | Chirale Synthesebausteine aus Aminosäuren: Dihydrothiazol-Derivate (Δ4-Thiazoline) aus Cystein |
| title_fullStr | Chirale Synthesebausteine aus Aminosäuren: Dihydrothiazol-Derivate (Δ4-Thiazoline) aus Cystein |
| title_full_unstemmed | Chirale Synthesebausteine aus Aminosäuren: Dihydrothiazol-Derivate (Δ4-Thiazoline) aus Cystein |
| title_short | Chirale Synthesebausteine aus Aminosäuren: Dihydrothiazol-Derivate (Δ4-Thiazoline) aus Cystein |
| title_sort | chirale synthesebausteine aus aminosauren dihydrothiazol derivate δ4 thiazoline aus cystein |
| url | https://www.chimia.ch/chimia/article/view/9925 |
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