Low-temperature oxyanion-accelerated vinylcyclopropane-cyclopentene rearrangement. Reaction of 2-(2-(trimethylsilyl)-ethenyl)cyclopropyl acetates with methyl lithium
Tetrahedron letters Volume 38 Issue 18
Page 3257-3260
published_at 1997-05-05
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| File | |
| Title ( eng ) |
Low-temperature oxyanion-accelerated vinylcyclopropane-cyclopentene rearrangement. Reaction of 2-(2-(trimethylsilyl)-ethenyl)cyclopropyl acetates with methyl lithium
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| Creator |
Sakurama Keiki
Yoshii Eiichi
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| Source Title |
Tetrahedron letters
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| Volume | 38 |
| Issue | 18 |
| Start Page | 3257 |
| End Page | 3260 |
| Abstract |
Reactions of four diastereomeric 2-(2-(trimethylsilyl)ethenyl)cyclopropyl acetates 7, derived from enol silyl ether 4 and Fischer carbene complex 6, with 2.2 equiv of MeLi at -80 ° to -30 °C afforded cyclopentenol 8 as a single diastereomer and acyclic enol silyl ethers 9 via the corresponding cyclopropanolates in ratios depending on the vinylsilane geometry. Predominant formation of 8 over 9 from (Z)-7 irrespective of the stereochemistry at C-1 was observed. This is the first example of oxyanion-accelerated vinylcyclopropane-cyclopentene rearrangement which proceeds at unprecedentedly low temperatures.
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| Keywords |
vinylcyclopropane-cyclopentene
low temperature
2-(2-(trimethylsilyl)ethenyl)cyclopropyl
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| NDC |
Chemistry [ 430 ]
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| Language |
eng
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| Resource Type | journal article |
| Publisher |
Elsevier Science Ltd.
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| Date of Issued | 1997-05-05 |
| Rights |
Copyright (c) 1997 Elsevier Science Ltd.
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| Publish Type | Author’s Original |
| Access Rights | open access |
| Source Identifier |
[ISSN] 0040-4039
[DOI] http://dx.doi.org/10.1016/S0040-4039(97)00579-0
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