Diels-Alder reaction of α-substituted acrylates and α-(methylene)lactones: Conformation of dienophiles and endo/exo selectivity
Tetrahedron Volume 50 Issue 27
Page 10839-10848
published_at 1994
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| File | |
| Title ( eng ) |
Diels-Alder reaction of α-substituted acrylates and α-(methylene)lactones: Conformation of dienophiles and endo/exo selectivity
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| Creator |
Imaoka Ikuhiro
Yoshii Eiichi
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| Source Title |
Tetrahedron
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| Volume | 50 |
| Issue | 27 |
| Start Page | 10839 |
| End Page | 10848 |
| Abstract |
to 7- and 9 to 11-membered α-(methylene)lactones has been carried out to examine correlation of dienophile structure with endo/exo selectivity. While the conformationally flexible acrylates produced cycloadducts of endo/exo = 59:41 to 74:26, the 5 to 7-membered lactones with rigid s-cis conjugated system provided cycloadducts of endo/exo = 13:87 to 32:68 and the 9 to 11-membered lactones which can take both s-cis and s-trans conformation afforded endo/exo ratios of 37:63 to 57:43
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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 | 1994 |
| Rights |
Copyright (c) 1994 Elsevier Science Ltd
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| Publish Type | Author’s Original |
| Access Rights | open access |
| Source Identifier |
[ISSN] 0040-4020
[DOI] 10.1016/S0040-4020(01)85696-9
[DOI] http://dx.doi.org/10.1016/S0040-4020(01)85696-9
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