Organic Letters 2009-08-20

Domino synthesis of bridged bicyclic tetrahydro-1,2-oxazines: access to stereodefined 4-aminocyclohexanols.

Dwayne A Dias, Michael A Kerr

Index: Org. Lett. 11(16) , 3694-7, (2009)

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Abstract

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.