Synthesis of Chiral Amino Alcohols Embodying the Bispidine Framework and Their Application as Ligands in Enantioselectively Catalyzed Additions to CO and CC Groups

✍ Scribed by Jan Spieler; Oliver Huttenloch; Herbert Waldmann

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 358 KB
• Volume: 2000
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(200002)2000:3<391::aid-ejoc391>3.0.co;2-r

✦ Synopsis

Two generally applicable routes for the synthesis of chiral amino alcohols embodying the bispidine framework have been developed. In linear route A the bispidine framework is built up successively from chiral primary amines via intermediate formation of a piperidinone and a bispidinone. In convergent route B an achiral bispidine is formed first and then the N-substituents are introduced by reaction of the nitrogen bases with chiral electrophiles. In order to determine if the bispidine core and its N-substituents can influence the steric course of enantioselective transformations, bispidine amino alcohols built up by these