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, 356 (11-12), 2697-2702

6-Azabicyclo[3.2.1]octanes Via Copper-Catalyzed Enantioselective Alkene Carboamination

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6-Azabicyclo[3.2.1]octanes Via Copper-Catalyzed Enantioselective Alkene Carboamination

Barbara J Casavant et al. Adv Synth Catal.

Abstract

Bridged bicyclic rings containing nitrogen heterocycles are important motifs in bioactive small organic molecules. An enantioselective copper-catalyzed alkene carboamination reaction that creates bridged heterocycles is reported herein. Two new rings are formed in this alkene carboamination reaction where N-sulfonyl-2-aryl-4-pentenamines are converted to 6-azabicyclo[3.2.1]octanes using [Ph-Box-Cu](OTf)2 or related catalysts in the presence of MnO2 as stoichiometric oxidant in moderate to good yields and generally excellent enantioselectivities. Two new stereocenters are formed in the reaction, and the C-C bond-forming arene addition is a net C-H functionalization.

Keywords: 6-azabicyclo[3.2.1]octane; alkaloids; carboamination; copper-catalyzed; enantioselective.

Figures

Figure 1
Figure 1
X-ray crystal structure of 3b (CCDC 991873).
Scheme 1
Scheme 1
Possible carboamination pathways.
Scheme 2
Scheme 2
Desymmetrization reactions.
Scheme 3
Scheme 3
Proposed catalytic cycle.

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