Highly efficient preparation of optically active 5-hydroxy-3-oxoesters by enantioselective reaction of diketene with aldehydes promoted by novel chiral Schiff base-titanium alkoxide complexes

✍ Scribed by Masahiko Hayashi; Kiyoshi Tanaka; Nobuki Oguni

• Book ID: 103977211
• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 199 KB
• Volume: 6
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/0957-4166(95)00230-m

✦ Synopsis

Optically active 5-hydroxy-3-oxoesters 1 can be obtained in up to 91% enantiomeric excess (e.e.) by the enantioselective reaction of diketene with aldehydes promoted by novel chiral Schiff base,---titanium alkoxide complexes.

Optically active derivatives 1 can be converted into 6-substituted 4-hydroxy lactones which are common structual components of compactin and mevinolin known as inhibitors of 3-hydroxy-3-methylglutaryl Coenzyme A (HMG-CoA) reductase. ! So far, several methods have been reported to synthesize optically active