Chiral Borated Esters in Asymmetric Synthesis: 1. The First Asymmetric Reaction Catalyzed by Chiral Spiroborated Esters with an O3BN Framework

• 来源期刊: 中国化学（英文版）
• 年，卷（期）: 2004,（11）
• 页码范围: 1336-1340
• 页数: 5页
• 语种: 英文

摘要

The first asymmetric reaction catalyzed by chiral spiroborated esters with an O3BN framework was reported. In the presence of 0.1 equivalent of (R,S)-1 or (S,S)-1, acetophenone was reduced by 0.6 equivalent of borane in THF at 0-5 ℃ for 2 h to give (R)-1-phenylethanol of up to 76% ee and 73% isolated yield. Influence of reaction conditions on the stereoselectivity of the reduction was investigated and a possible catalytic mechanism of the chiral spiroborated esters toward the reduction was also suggested.