diasetereoselective allylation of chiral glyoxylic oxime ethers and reduction of N-phenyl camphorpyrazolidinone derived a-keto amides

• Main Author: 辜卡力
• Other Authors: 陳焜銘
• Format: Others
• Language: zh-TW
• Published: 2006
• Online Access: http://ndltd.ncl.edu.tw/handle/27426717406539814429

博士 === 國立臺灣師範大學 === 化學系 === 94 === In the first part of this monograph, various chiral glyoxylic oximes were prepared to develop a new route to synthesize chiral α-amino amides, which are synthetic intermidiates of α-amino acids. The allylation of camphor sultam derived glyoxylic oxime ether by allyltributyltin in the presence of Lewis acids Zn(OTf)2, AgOTf, Sn(OTf)2 provided homoallylic α-amino amides, and Sn(OTf)2 emerged as the best Lewis acid when tested in allylation of various chiral glyoxylic oxime ethers. To continue the research in allylation of glyoxylic oxime ether, we studied allylation by using triallylaluminium. The reaction of triallylaluminium with chiral glyoxylic oxime ethers provided homoallylic amine products up to > 99% diastereoselectivity. In the following parts, we have investigated the scope of N-phenyl camphorpyrazolidinone in synthetic organic chemistry. When N-phenyl camphorpyrazolidinone derived α-keto amides employed in hydride reduction, the hydride reduction of aliphatic and aromatic α-keto amides provided corresponding α-hydroxy amides in excellent yields and very high level of diastereoselectivities.