Asymmetric synthesis of epoxides from aromatic aldehydes and benzyl halides catalyzed by C2 symmetric optically active sulfides having a binaphthyl skeleton

✍ Scribed by Yoshihiro Miyake; Arihiro Oyamada; Yoshiaki Nishibayashi; Sakae Uemura

• Book ID: 102230785
• Publisher: John Wiley and Sons
• Year: 2002
• Tongue: English
• Weight: 148 KB
• Volume: 13
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.10028

✦ Synopsis

Abstract

Reactions of aromatic aldehydes with benzyl bromide or iodide in the presence of a catalytic amount (10 mol%) of a C~2~ symmetric sulfide having a binaphthyl skeleton afford the corresponding trans‐stilbene oxides in moderate to good yields with moderate enantioselectivities (up to 55% enantiomeric excess). The addition of tetra‐n‐butylammonium iodide to the catalytic reaction system much improves the yield of the epoxides. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:270–275, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10028