COPPER-CATALYZED N-ACYLIMINIUM ION CYCLIZATION TO 3-AZABICYCLO[3.3.1]NONANES - SYNTHESIS OF 2,4-DISUBSTITUTED 1-AZA-ADAMANTANES

Authors
UDDING JH PAPIN N HIEMSTRA H SPECKAMP WN
Citation
Jh. Udding et al., COPPER-CATALYZED N-ACYLIMINIUM ION CYCLIZATION TO 3-AZABICYCLO[3.3.1]NONANES - SYNTHESIS OF 2,4-DISUBSTITUTED 1-AZA-ADAMANTANES, Tetrahedron, 50(29), 1994, pp. 8853-8862
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
29
Year of publication
1994
Pages
8853 - 8862
Database
ISI
SICI code
0040-4020(1994)50:29<8853:CNICT3>2.0.ZU;2-L
Abstract
An efficient Cu(bpy)Cl-catalysed N-acyliminium ion cyclisation to N-pr otected 3-azabicyclo[3.3.1]non-6-ene is reported. This compound has be en demonstrated to be a valuable intermediate in the synthesis of 2,4- disubstituted 1-aza-adamantanes, and led to a stereoselective synthesi s of 1-aza-adamantan-4-ol. This selectivity was also observed in the s ynthesis of two a-amino acid derivatives with the adamantane skeleton. An X-ray crystal structure of one of the cyclisation products is pres ented.