α-Alkylation of (S)-Glyceric Acid through the tert-Butylthioester of (2R,4S)-2-tert-Butyl-1,3-dioxolane-4-carboxylic Acid
The thioester (9) mentioned in the title is prepared in three steps from (S)-serine. Deprotonation with LiN(CHMe2)2 generates a chiral enolate (10) which is alkylated preferentially from the Re-face (cis to the tert-butyl group), to give products of type 11. Possible reasons for the steric course o...
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| Format: | Article |
| Language: | deu |
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Swiss Chemical Society
1985-01-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9642 |
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| _version_ | 1850283835229470720 |
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| author | Dieter Seebach Marlyse Coquoz |
| author_facet | Dieter Seebach Marlyse Coquoz |
| author_sort | Dieter Seebach |
| collection | DOAJ |
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The thioester (9) mentioned in the title is prepared in three steps from (S)-serine. Deprotonation with LiN(CHMe2)2 generates a chiral enolate (10) which is alkylated preferentially from the Re-face (cis to the tert-butyl group), to give products of type 11. Possible reasons for the steric course of the reaction of the thioester enolate (relative topicity lk, see 13) and the value of the products thus available as synthetic building blocks with a persubstituted, OH-functionalized asymmetric carbon atom (see 4, 5, 6) are discussed.
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| format | Article |
| id | doaj-art-a1c4223afbde4af7bb8d460ff3f1422a |
| institution | OA Journals |
| issn | 0009-4293 2673-2424 |
| language | deu |
| publishDate | 1985-01-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj-art-a1c4223afbde4af7bb8d460ff3f1422a2025-08-20T01:47:41ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24241985-01-0139110.2533/chimia.1985.20α-Alkylation of (S)-Glyceric Acid through the tert-Butylthioester of (2R,4S)-2-tert-Butyl-1,3-dioxolane-4-carboxylic AcidDieter Seebach0Marlyse Coquoz1Laboratorium 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 The thioester (9) mentioned in the title is prepared in three steps from (S)-serine. Deprotonation with LiN(CHMe2)2 generates a chiral enolate (10) which is alkylated preferentially from the Re-face (cis to the tert-butyl group), to give products of type 11. Possible reasons for the steric course of the reaction of the thioester enolate (relative topicity lk, see 13) and the value of the products thus available as synthetic building blocks with a persubstituted, OH-functionalized asymmetric carbon atom (see 4, 5, 6) are discussed. https://www.chimia.ch/chimia/article/view/9642 |
| spellingShingle | Dieter Seebach Marlyse Coquoz α-Alkylation of (S)-Glyceric Acid through the tert-Butylthioester of (2R,4S)-2-tert-Butyl-1,3-dioxolane-4-carboxylic Acid CHIMIA |
| title | α-Alkylation of (S)-Glyceric Acid through the tert-Butylthioester of (2R,4S)-2-tert-Butyl-1,3-dioxolane-4-carboxylic Acid |
| title_full | α-Alkylation of (S)-Glyceric Acid through the tert-Butylthioester of (2R,4S)-2-tert-Butyl-1,3-dioxolane-4-carboxylic Acid |
| title_fullStr | α-Alkylation of (S)-Glyceric Acid through the tert-Butylthioester of (2R,4S)-2-tert-Butyl-1,3-dioxolane-4-carboxylic Acid |
| title_full_unstemmed | α-Alkylation of (S)-Glyceric Acid through the tert-Butylthioester of (2R,4S)-2-tert-Butyl-1,3-dioxolane-4-carboxylic Acid |
| title_short | α-Alkylation of (S)-Glyceric Acid through the tert-Butylthioester of (2R,4S)-2-tert-Butyl-1,3-dioxolane-4-carboxylic Acid |
| title_sort | α alkylation of s glyceric acid through the tert butylthioester of 2r 4s 2 tert butyl 1 3 dioxolane 4 carboxylic acid |
| url | https://www.chimia.ch/chimia/article/view/9642 |
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