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Asymmetric Synthesis of β-Hydroxy Sulfides Controlled by Remote Sulfoxides
Reactions of (S)-α-(methylthio)-2-(p-tolylsulfinyl)benzyl carbanion with different carbonyl compounds proceeds with complete control of the configuration at the benzylic position. Aldehydes yield easily separable mixtures of β-hydroxy sulfides, epimers at the hydroxylic carbon, where the stereoselec...
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| Published in: | Journal of organic chemistry 2007-02, Vol.72 (3), p.1035-1038 |
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| Main Authors: | , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-a381t-1a15b37c27d0f58451cb90e610aa117d52e0ea3a4743665f9ed9f875c4846ad93 |
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| cites | cdi_FETCH-LOGICAL-a381t-1a15b37c27d0f58451cb90e610aa117d52e0ea3a4743665f9ed9f875c4846ad93 |
| container_end_page | 1038 |
| container_issue | 3 |
| container_start_page | 1035 |
| container_title | Journal of organic chemistry |
| container_volume | 72 |
| creator | Arroyo, Yolanda Rodríguez, J. Félix Santos, Mercedes Sanz Tejedor, M. Ascensión García Ruano, José Luis |
| description | Reactions of (S)-α-(methylthio)-2-(p-tolylsulfinyl)benzyl carbanion with different carbonyl compounds proceeds with complete control of the configuration at the benzylic position. Aldehydes yield easily separable mixtures of β-hydroxy sulfides, epimers at the hydroxylic carbon, where the stereoselectivity depends on steric factors (from 20% to >98% de). |
| doi_str_mv | 10.1021/jo062053q |
| format | article |
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| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2007-02, Vol.72 (3), p.1035-1038 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_68954969 |
| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Benzene Derivatives - chemistry Carbonates - chemistry Chemistry Exact sciences and technology Models, Chemical Organic chemistry Stereoisomerism Sulfhydryl Compounds - chemistry Sulfides - chemical synthesis Sulfonium Compounds - chemistry Sulfoxides - chemistry |
| title | Asymmetric Synthesis of β-Hydroxy Sulfides Controlled by Remote Sulfoxides |
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