[3+2] Cascade Ring-Closing/Ring-Opening Strategy: Access to N-Indene-Tethered Amino Alcohols

An unprecedented atom-economic redox neutral regioselective Rh-(III)-catalyzed cascade [3+2] annulation of 2-aryl oxazoline with alpha,beta-unsaturated nitro olefins has been accomplished, furnishing a novel set of nitro-functionalized indene-tethered amino alcohols through a synergistic ring-closing/ring-opening strategy via the formation of two new C-C bonds and the regioselective cleavage of the C2-O bond of oxazoline under silver free mild reaction conditions with a broad substrate scope.

Automated summary

An unprecedented atom-economic and redox-neutral regioselective cascade [3+2] annulation reaction of 2-aryl oxazoline with alpha,beta-unsaturated nitro olefins has been achieved using a Rh-(III) catalyst. This reaction provides a novel set of nitro-functionalized indene-tethered amino alcohols through a synergistic ring-closing/ring-opening strategy, involving the formation of two new C-C bonds and the regioselective cleavage of the C2-O bond of oxazoline. The reaction can be conducted under silver-free mild reaction conditions and exhibits a broad substrate scope.