Journal
ORGANIC LETTERS
Volume 12, Issue 24, Pages 5608-5611Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol102605q
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Funding
- Ministerio de Ciencia e Innovacion (MICINN) [CTQ2009-07791]
- Consejeria de Educacion de la Comunidad de Madrid [S2009/PPQ-1634]
- Universidad Autonoma de Madrid/Comunidad de Madrid (UAM/CAM ) [CCG08-UAM/PPQ-4454]
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An efficient Cu(I)-catalyzed asymmetric [3 + 2] cycloaddition of N-(2-pyridylmethyl) imines has been developed. In the presence of a Cu(CH3CN)(4)PF6/bisoxazoline catalyst system, high levels of enantioselectivity (up to 97% ee) and moderate to high exo selectivity were achieved with a wide variety of substituted dipolarophiles, including maleimides, fumarates, fumarodinitrile, enones, and nitroalkenes. The reaction with unsymmetrically substituted dipolarophiles is completely regioselective.
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