Asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-ene carboxylate
An expeditious asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-enecarboxylate has been achieved in four steps in 42% overall yield employing as the key step a domino reaction initiated by a highly diastereoselective lithium amide 1,4-conjugate addition to a nona-2,7-diendioic diester follo...
| Main Authors: | , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2006
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| _version_ | 1826282774228631552 |
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| author | Garrido, N Diez, D Dominguez, S Garcia, M Sanchez, MR Davies, S |
| author_facet | Garrido, N Diez, D Dominguez, S Garcia, M Sanchez, MR Davies, S |
| author_sort | Garrido, N |
| collection | OXFORD |
| description | An expeditious asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-enecarboxylate has been achieved in four steps in 42% overall yield employing as the key step a domino reaction initiated by a highly diastereoselective lithium amide 1,4-conjugate addition to a nona-2,7-diendioic diester followed by a 6-exo-trig cyclisation of the thus formed enolate. Cope elimination protocol of the cyclic adduct affords, depending on the lithium amide used, the corresponding nitro-compound or the expected cyclohexene derivative. The methyl group attached to the cyclohexane ring is achieved by selective ester hydrolysis and subsequent Barton decarboxylation. © 2006 Elsevier Ltd. All rights reserved. |
| first_indexed | 2024-03-07T00:48:55Z |
| format | Journal article |
| id | oxford-uuid:85ae1cb0-c375-4a52-a9df-454de94b5618 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T00:48:55Z |
| publishDate | 2006 |
| record_format | dspace |
| spelling | oxford-uuid:85ae1cb0-c375-4a52-a9df-454de94b56182022-03-26T21:59:11ZAsymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-ene carboxylateJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:85ae1cb0-c375-4a52-a9df-454de94b5618EnglishSymplectic Elements at Oxford2006Garrido, NDiez, DDominguez, SGarcia, MSanchez, MRDavies, SAn expeditious asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-enecarboxylate has been achieved in four steps in 42% overall yield employing as the key step a domino reaction initiated by a highly diastereoselective lithium amide 1,4-conjugate addition to a nona-2,7-diendioic diester followed by a 6-exo-trig cyclisation of the thus formed enolate. Cope elimination protocol of the cyclic adduct affords, depending on the lithium amide used, the corresponding nitro-compound or the expected cyclohexene derivative. The methyl group attached to the cyclohexane ring is achieved by selective ester hydrolysis and subsequent Barton decarboxylation. © 2006 Elsevier Ltd. All rights reserved. |
| spellingShingle | Garrido, N Diez, D Dominguez, S Garcia, M Sanchez, MR Davies, S Asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-ene carboxylate |
| title | Asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-ene carboxylate |
| title_full | Asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-ene carboxylate |
| title_fullStr | Asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-ene carboxylate |
| title_full_unstemmed | Asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-ene carboxylate |
| title_short | Asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-ene carboxylate |
| title_sort | asymmetric synthesis of pent 3 yl r 6 methyl cyclohex 1 ene carboxylate |
| work_keys_str_mv | AT garridon asymmetricsynthesisofpent3ylr6methylcyclohex1enecarboxylate AT diezd asymmetricsynthesisofpent3ylr6methylcyclohex1enecarboxylate AT dominguezs asymmetricsynthesisofpent3ylr6methylcyclohex1enecarboxylate AT garciam asymmetricsynthesisofpent3ylr6methylcyclohex1enecarboxylate AT sanchezmr asymmetricsynthesisofpent3ylr6methylcyclohex1enecarboxylate AT daviess asymmetricsynthesisofpent3ylr6methylcyclohex1enecarboxylate |