Activation of Styrenes Towards Diels-Alder Cycloadditions by Osmium(II): Synthesis of Stereodefined Decalin Ring Systems

Kolis, S. P.; Chordia, M. D.; Liu, R.; E., K. M.; Harman, W. D. Activation of Styrenes Towards Diels-Alder Cycloadditions by Osmium(II): Synthesis of Stereodefined Decalin Ring Systems. J. Am. Chem. Soc. 1998, 120, 2218.

Abstract

The complex [Os(NH3)52-anisole)]2+ reacts with acetals or Michael acceptors to form 4-methoxystyrene complexes that are exclusively coordinated at the arene (η2). These styrene complexes are active dienes and readily participate in Diels−Alder reactions with electron-deficient olefins to form tetrahydronaphthalene complexes. The cycloadducts are formed typically as single diastereomers and are valuable as precursors to functionalized tetralins and decalins.

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