Highly Regioselective Pd-Catalyzed Intermolecular Aminoacetoxylation of Alkenes and Evidence for cis-Aminopalladation and SN2 C-O Bond Formation

Guosheng Liu and Shannon S. Stahl*

*Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, Email: stahlchem.wisc.edu

G. Liu, S. S. Stahl, J. Am. Chem. Soc., 2006, 128, 7179-7181.

DOI: 10.1021/ja061706h (free Supporting Information)

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Abstract

An intermolecular Pd-catalyzed aminoacetoxylation of alkenes with phthalimide as the nitrogen source and PhI(OAc)₂ as the stoichiometric oxidant and source of acetate achieves a highly regio- and diastereoselective oxidative 1,2-difunctionalization of alkenes. The mechanism is discussed.

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proposed mechanism

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Key Words

β-Amino alcohols, Iodosobenzene diacetate, Multicomponent Reactions, Phthalimides

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ID: J48-Y2006-2090