Domino synthesis of bridged bicyclic tetrahydro-1,2-oxazines: access to stereodefined 4-aminocyclohexanols.
The intramolecular variant of the homo-[3 + 2]-dipolar cycloaddition of nitrones (generated in situ from an aldehyde and a hydroxylamine) with donor-acceptor cyclopropanes allows for the efficient synthesis of bridged tetrahydro-1,2-oxazines. This domino sequence produces adducts amenable to reductive N-O bond cleavage producing cis-1,4-aminocyclohexanols in excellent yields.
Dias
Dwayne A
DA
Department of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7.
Kerr
Michael A
MA
D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry; D003514:Cyclohexylamines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003511:Cyclohexanols; D003514:Cyclohexylamines; D010078:Oxazines; C063934:4-aminocyclohexanol