d<sup>5</sup>‐Reactions of Doubly Deprotonated γ,δ‐Unsaturated Carbonyl Derivatives with Electrophiles. A Novel Approach to the Synthesis of Tetrahydrofuran and Tetrahydropyran Derivatives
The dienone‐dianion derivatives 1 react with all types of electrophiles tested (alkyl halide, silyl chloride, ester, ketone, aldehyde, epoxide) to give β, γ‐unsaturated carbonyl compounds of type A (see Formulae 2–6, 13, 14 and Tables 1–5). The α‐ and β‐hydroxyalkylation products obtained from 1a–1d...
Saved in:
| Main Authors: | , , , , , |
|---|---|
| Other Authors: | |
| Format: | Article |
| Published: |
2018
|
| Subjects: | |
| Online Access: | https://repository.li.mahidol.ac.th/handle/123456789/30308 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Institution: | Mahidol University |
| id |
th-mahidol.30308 |
|---|---|
| record_format |
dspace |
| spelling |
th-mahidol.303082018-10-12T14:29:29Z d<sup>5</sup>‐Reactions of Doubly Deprotonated γ,δ‐Unsaturated Carbonyl Derivatives with Electrophiles. A Novel Approach to the Synthesis of Tetrahydrofuran and Tetrahydropyran Derivatives Dieter Seebach Manat Pohmakotr Christian Schregenberger Beat Weidmann Raghao S. Mali Srisuke Pohmakotr ETH Zurich Justus Liebig University Giessen Mahidol University Biochemistry, Genetics and Molecular Biology Chemical Engineering Chemistry Pharmacology, Toxicology and Pharmaceutics The dienone‐dianion derivatives 1 react with all types of electrophiles tested (alkyl halide, silyl chloride, ester, ketone, aldehyde, epoxide) to give β, γ‐unsaturated carbonyl compounds of type A (see Formulae 2–6, 13, 14 and Tables 1–5). The α‐ and β‐hydroxyalkylation products obtained from 1a–1d can be converted to tetra‐hydrofuran and tetrahydropyran derivatives 7 and 16, respectively (Tables 1 and 2), those from the sulfur analogues 1e and 1f to ketene thioacetals 9 and to dienone derivatives 10 and 12. The t‐butyl and α‐hydroxy‐ketones are cleaved to give nitriles, amides, carboxylic acids and esters (Formulae 16‐25). The reagents 1 allow to synthesize products with distant functional groups in one step (cf. 1,8‐diketones 14 and Formulae 26–30); they correspond to the d5‐synthons 31–33; in Table 6, they are compared with other d5‐reagents. Copyright © 1982 Verlag GmbH & Co. KGaA, Weinheim 2018-10-12T07:25:43Z 2018-10-12T07:25:43Z 1982-01-01 Article Helvetica Chimica Acta. Vol.65, No.2 (1982), 419-450 10.1002/hlca.19820650202 15222675 0018019X 2-s2.0-84985108005 https://repository.li.mahidol.ac.th/handle/123456789/30308 Mahidol University SCOPUS https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84985108005&origin=inward |
| institution |
Mahidol University |
| building |
Mahidol University Library |
| continent |
Asia |
| country |
Thailand Thailand |
| content_provider |
Mahidol University Library |
| collection |
Mahidol University Institutional Repository |
| topic |
Biochemistry, Genetics and Molecular Biology Chemical Engineering Chemistry Pharmacology, Toxicology and Pharmaceutics |
| spellingShingle |
Biochemistry, Genetics and Molecular Biology Chemical Engineering Chemistry Pharmacology, Toxicology and Pharmaceutics Dieter Seebach Manat Pohmakotr Christian Schregenberger Beat Weidmann Raghao S. Mali Srisuke Pohmakotr d<sup>5</sup>‐Reactions of Doubly Deprotonated γ,δ‐Unsaturated Carbonyl Derivatives with Electrophiles. A Novel Approach to the Synthesis of Tetrahydrofuran and Tetrahydropyran Derivatives |
| description |
The dienone‐dianion derivatives 1 react with all types of electrophiles tested (alkyl halide, silyl chloride, ester, ketone, aldehyde, epoxide) to give β, γ‐unsaturated carbonyl compounds of type A (see Formulae 2–6, 13, 14 and Tables 1–5). The α‐ and β‐hydroxyalkylation products obtained from 1a–1d can be converted to tetra‐hydrofuran and tetrahydropyran derivatives 7 and 16, respectively (Tables 1 and 2), those from the sulfur analogues 1e and 1f to ketene thioacetals 9 and to dienone derivatives 10 and 12. The t‐butyl and α‐hydroxy‐ketones are cleaved to give nitriles, amides, carboxylic acids and esters (Formulae 16‐25). The reagents 1 allow to synthesize products with distant functional groups in one step (cf. 1,8‐diketones 14 and Formulae 26–30); they correspond to the d5‐synthons 31–33; in Table 6, they are compared with other d5‐reagents. Copyright © 1982 Verlag GmbH & Co. KGaA, Weinheim |
| author2 |
ETH Zurich |
| author_facet |
ETH Zurich Dieter Seebach Manat Pohmakotr Christian Schregenberger Beat Weidmann Raghao S. Mali Srisuke Pohmakotr |
| format |
Article |
| author |
Dieter Seebach Manat Pohmakotr Christian Schregenberger Beat Weidmann Raghao S. Mali Srisuke Pohmakotr |
| author_sort |
Dieter Seebach |
| title |
d<sup>5</sup>‐Reactions of Doubly Deprotonated γ,δ‐Unsaturated Carbonyl Derivatives with Electrophiles. A Novel Approach to the Synthesis of Tetrahydrofuran and Tetrahydropyran Derivatives |
| title_short |
d<sup>5</sup>‐Reactions of Doubly Deprotonated γ,δ‐Unsaturated Carbonyl Derivatives with Electrophiles. A Novel Approach to the Synthesis of Tetrahydrofuran and Tetrahydropyran Derivatives |
| title_full |
d<sup>5</sup>‐Reactions of Doubly Deprotonated γ,δ‐Unsaturated Carbonyl Derivatives with Electrophiles. A Novel Approach to the Synthesis of Tetrahydrofuran and Tetrahydropyran Derivatives |
| title_fullStr |
d<sup>5</sup>‐Reactions of Doubly Deprotonated γ,δ‐Unsaturated Carbonyl Derivatives with Electrophiles. A Novel Approach to the Synthesis of Tetrahydrofuran and Tetrahydropyran Derivatives |
| title_full_unstemmed |
d<sup>5</sup>‐Reactions of Doubly Deprotonated γ,δ‐Unsaturated Carbonyl Derivatives with Electrophiles. A Novel Approach to the Synthesis of Tetrahydrofuran and Tetrahydropyran Derivatives |
| title_sort |
d<sup>5</sup>‐reactions of doubly deprotonated γ,δ‐unsaturated carbonyl derivatives with electrophiles. a novel approach to the synthesis of tetrahydrofuran and tetrahydropyran derivatives |
| publishDate |
2018 |
| url |
https://repository.li.mahidol.ac.th/handle/123456789/30308 |
| _version_ |
1763491480224137216 |