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Efficient catalytic enantioselective synthesis of unsaturated amines: preparation of small- and medium-ring cyclic amines through mo-catalyzed asymmetric ring-closing metathesis in the absence of solvent
Authors:Dolman Sarah J  Sattely Elizabeth S  Hoveyda Amir H  Schrock Richard R
Institution:Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Abstract:The first catalytic asymmetric ring-closing metathesis method for the synthesis of N-containing heterocycles is reported; this is accomplished through Mo-catalyzed kinetic resolution or desymmetrization of unsaturated amines. Importantly, this catalytic asymmetric method delivers medium-ring unsaturated amines (including eight-membered rings) in high yield, with exceptional enantioselectivity and without the need for solvents. These enantioselective reactions can be effected by catalysts prepared in situ from commercially available reagents.
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