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Facile reduction of tertiary lactams to cyclic amines with 9-borabicyclo[3.3.1]nonane (9-BBN)

Christopher J. Collins, M. Lanz, Bakthan Singaram

*Department of Chemistry and Biochemistry, University of California, Santa Cruz, 1156 High Street, Santa Cruz, California, 95064, Email:

C. J. Collins, M. Lanz, B. Singaram, Tetrahedron Lett., 1999, 40, 3673-3676.

DOI: 10.1016/S0040-4039(99)00556-0

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Using 2.2 to 2.5 equivalents of 9-borabicyclo[3.3.1]nonane (9-BBN), various 5- and 6-membered tertiary lactams were chemoselectively reduced to the corresponding cyclic tertiary amines. The reaction tolerates the presence of an ester.

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Key Words

9-borabicyclo[3.3.1]nonane, reduction of amides, pyrrolidines

ID: J72-Y1999