Lipase-catalyzed enantioselective desymmetrization of prochiral 3,3-bis(hydroxymethyl)oxindoles

✍ Scribed by Shuji Akai; Toshiaki Tsujino; Tadaatsu Naka; Kouichi Tanimoto; Yasuyuki Kita

• Book ID: 104231596
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 62 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01547-7

✦ Synopsis

Oxindoles 3b-d (91-98% ee) having a chiral quaternary carbon center at the C-3 position were prepared from readily available oxindoles 5a-c in 50-64% overall yields, in which an enantioselective desymmetrization of prochiral 1,3-diols 2b-d using a Candida rugosa lipase (Meito OF) and 1-ethoxyvinyl 2-furoate 1 was employed as the key step.