Details
| Original language | English |
|---|---|
| Pages (from-to) | 1811-1821 |
| Number of pages | 11 |
| Journal | Liebigs Annales |
| Issue number | 11 |
| Publication status | Published - 22 Oct 1996 |
| Externally published | Yes |
Abstract
1,3-Functionalized cyclopentanes, -hexanes and -heptanes are obtained by addition of lithiated silyldithioacetals 7 to epoxyhomoallyl tosylates 4-6. The reaction involves a cascade of epoxide ring opening, of Brook 1,4-rearrangement and tosylate substitution. The method is particularly suitable for the preparation of cyclopentanes, whereas cyclohexanes and -heptanes are formed in yields only up to 49%. Use of enantiomerically pure epoxides provides optically active cyclopentanes (S)-10b, d, 11a as well as oxetanes (S)-14a, b. Hydrolysis of the dithioacetal function leads to the corresponding ketones 12. Cyclization of epoxide 24b gives an anellated cyclopentane 26, the configuration of which was established by X-ray structural analysis of dinitrobenzoate 27. Use of epoxide 29b provides the anellated tetrahydrofuran 30.
Keywords
- Domino reaction, Functionalized cyclopentanes, -hexanes and -heptanes, Oxetanes, Tetrahydrofurans
ASJC Scopus subject areas
- Chemistry(all)
- General Chemistry
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In: Liebigs Annales, No. 11, 22.10.1996, p. 1811-1821.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthesis of functionalized cyclopentanes, cyclohexanes and cycloheptanes by a silicon-induced domino reaction
AU - Michel, Tycho
AU - Kirschning, Andreas
AU - Beier, Christian
AU - Bräuer, Nico
AU - Schaumann, Ernst
AU - Adiwidjaja, Gunadi
PY - 1996/10/22
Y1 - 1996/10/22
N2 - 1,3-Functionalized cyclopentanes, -hexanes and -heptanes are obtained by addition of lithiated silyldithioacetals 7 to epoxyhomoallyl tosylates 4-6. The reaction involves a cascade of epoxide ring opening, of Brook 1,4-rearrangement and tosylate substitution. The method is particularly suitable for the preparation of cyclopentanes, whereas cyclohexanes and -heptanes are formed in yields only up to 49%. Use of enantiomerically pure epoxides provides optically active cyclopentanes (S)-10b, d, 11a as well as oxetanes (S)-14a, b. Hydrolysis of the dithioacetal function leads to the corresponding ketones 12. Cyclization of epoxide 24b gives an anellated cyclopentane 26, the configuration of which was established by X-ray structural analysis of dinitrobenzoate 27. Use of epoxide 29b provides the anellated tetrahydrofuran 30.
AB - 1,3-Functionalized cyclopentanes, -hexanes and -heptanes are obtained by addition of lithiated silyldithioacetals 7 to epoxyhomoallyl tosylates 4-6. The reaction involves a cascade of epoxide ring opening, of Brook 1,4-rearrangement and tosylate substitution. The method is particularly suitable for the preparation of cyclopentanes, whereas cyclohexanes and -heptanes are formed in yields only up to 49%. Use of enantiomerically pure epoxides provides optically active cyclopentanes (S)-10b, d, 11a as well as oxetanes (S)-14a, b. Hydrolysis of the dithioacetal function leads to the corresponding ketones 12. Cyclization of epoxide 24b gives an anellated cyclopentane 26, the configuration of which was established by X-ray structural analysis of dinitrobenzoate 27. Use of epoxide 29b provides the anellated tetrahydrofuran 30.
KW - Domino reaction
KW - Functionalized cyclopentanes, -hexanes and -heptanes
KW - Oxetanes
KW - Tetrahydrofurans
UR - http://www.scopus.com/inward/record.url?scp=33748907563&partnerID=8YFLogxK
U2 - 10.1002/jlac.199619961115
DO - 10.1002/jlac.199619961115
M3 - Article
AN - SCOPUS:33748907563
SP - 1811
EP - 1821
JO - Liebigs Annales
JF - Liebigs Annales
SN - 0947-3440
IS - 11
ER -