Studies on the generation of enolate anions from butane-2,3-diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides.
Highly diastereoselective coupling reactions of enolates derived from butane-2,3-diacetal protected glycolic acids 1 and 2 and their alkylated derivatives with aldehydes are reported together with their efficient acid-catalysed deprotection to yield enantiopure anti-2,3-dihydroxyesters. A procedure...
| Main Authors: | , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2004
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| _version_ | 1797105931181359104 |
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| author | Ley, S Dixon, D Guy, RT Palomero, M Polara, A Rodriguez, F Sheppard, T |
| author_facet | Ley, S Dixon, D Guy, RT Palomero, M Polara, A Rodriguez, F Sheppard, T |
| author_sort | Ley, S |
| collection | OXFORD |
| description | Highly diastereoselective coupling reactions of enolates derived from butane-2,3-diacetal protected glycolic acids 1 and 2 and their alkylated derivatives with aldehydes are reported together with their efficient acid-catalysed deprotection to yield enantiopure anti-2,3-dihydroxyesters. A procedure to provide the corresponding syn-2,3-dihydroxyesters is also described in two cases, proceeding via an acylation-reduction sequence. An usual double addition reaction of butane-2,3-diacetal protected glycolic acid to small aliphatic acid chlorides provides a synthetically useful, densely-functionalised lactone after acidic deprotection. |
| first_indexed | 2024-03-07T06:54:25Z |
| format | Journal article |
| id | oxford-uuid:fda3ecbc-11b0-41ed-bd29-12d6681d4b7e |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T06:54:25Z |
| publishDate | 2004 |
| record_format | dspace |
| spelling | oxford-uuid:fda3ecbc-11b0-41ed-bd29-12d6681d4b7e2022-03-27T13:30:26ZStudies on the generation of enolate anions from butane-2,3-diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:fda3ecbc-11b0-41ed-bd29-12d6681d4b7eEnglishSymplectic Elements at Oxford2004Ley, SDixon, DGuy, RTPalomero, MPolara, ARodriguez, FSheppard, THighly diastereoselective coupling reactions of enolates derived from butane-2,3-diacetal protected glycolic acids 1 and 2 and their alkylated derivatives with aldehydes are reported together with their efficient acid-catalysed deprotection to yield enantiopure anti-2,3-dihydroxyesters. A procedure to provide the corresponding syn-2,3-dihydroxyesters is also described in two cases, proceeding via an acylation-reduction sequence. An usual double addition reaction of butane-2,3-diacetal protected glycolic acid to small aliphatic acid chlorides provides a synthetically useful, densely-functionalised lactone after acidic deprotection. |
| spellingShingle | Ley, S Dixon, D Guy, RT Palomero, M Polara, A Rodriguez, F Sheppard, T Studies on the generation of enolate anions from butane-2,3-diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides. |
| title | Studies on the generation of enolate anions from butane-2,3-diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides. |
| title_full | Studies on the generation of enolate anions from butane-2,3-diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides. |
| title_fullStr | Studies on the generation of enolate anions from butane-2,3-diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides. |
| title_full_unstemmed | Studies on the generation of enolate anions from butane-2,3-diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides. |
| title_short | Studies on the generation of enolate anions from butane-2,3-diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides. |
| title_sort | studies on the generation of enolate anions from butane 2 3 diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides |
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