Microbiological enantioselective synthesis of ( S) and ( R) 4-( p-anisyloxy)-3-hydroxybutyrates as new chiral building blocks for the synthesis of β-lactam antibiotics

• Published in: Tetrahedron Vol. 50; no. 41; pp. 11983 - 11994
• Main Authors: Banfi, Luca, Cascio, Giuseppe, Ghiron, Chiara, Guanti, Giuseppe, Manghisi, Elso, Narisano, Enrica, Riva, Renata
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 1994
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/S0040-4020(01)89309-1

Both enantiomers of 4- p-anisyloxy-3-hydroxybutanoates 4 have been prepared in high e.e. by reduction of the corresponding β-ketoesters or β-ketocarboxylates with immobilized fermenting baker's yeast. The utility of these new chiral building blocks in the synthesis of pharmacologically important β-lactam antibiotics has been demonstrated. Reduction of β-ketoesters or β-ketocarboxylates 1 with immobilized baker's yeast gave ( R) or ( S) 2, as new useful chiral building blocks.