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...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2004-12, Vol.2 (24), p.3618-3627 |
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| container_issue | 24 |
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| container_title | Organic & biomolecular chemistry |
| container_volume | 2 |
| creator | Ley, Steven V Dixon, Darren J Guy, Richard T Palomero, Maria A Polara, Alessandra Rodriguez, Felix Sheppard, Tom D |
| 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. |
| doi_str_mv | 10.1039/b412790k |
| format | Article |
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A procedure to provide the corresponding syn-2,3-dihydroxyesters is also described in two cases, proceeding via an acylation-reduction sequence. 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A procedure to provide the corresponding syn-2,3-dihydroxyesters is also described in two cases, proceeding via an acylation-reduction sequence. 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| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2004-12, Vol.2 (24), p.3618-3627 |
| issn | 1477-0520 1477-0539 |
| language | eng |
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| source | Royal Society of Chemistry Journals Archive (1841-2007); MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Acetals - chemistry Acids - chemistry Aldehydes - chemistry Anions - chemical synthesis Hydrocarbons, Chlorinated - chemistry Ketones - chemical synthesis Molecular Conformation Stereoisomerism |
| 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 |
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