Rapid and Stereoselective C-C, C-O, C-N and C-S Couplings via Microwave Accelerated Palladium-Catalyzed Allylic Substitutions

Ulf Bremberg; Serghey Lutsenko; Nils-Fredrik Kaiser; Mats Larhed; Anders Hallberg; Christina Moberg

doi:10.1055/s-2000-6298

Synthesis 2000; 2000(7): 1004-1008
DOI: 10.1055/s-2000-6298

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Rapid and Stereoselective C-C, C-O, C-N and C-S Couplings via Microwave Accelerated Palladium-Catalyzed Allylic Substitutions

Ulf Bremberg^* , Serghey Lutsenko, Nils-Fredrik Kaiser, Mats Larhed, Anders Hallberg, Christina Moberg

^*Department of Chemistry, Organic Chemistry, Royal Institute of Technology, SE-100 44 Stockholm, Sweden; Fax +46(8)7912333; E-mail: kimo@orgchem.kth.se

Abstract

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Palladium-catalyzed substitution of cyclohex-2-en-1-yl ethyl carbonate with neutral C-, O-, and N-nucleophiles was achieved in 1 - 2 minutes using microwave flash heating. Enantioselectivities up to 96% were observed. Ionic nucleophiles tended to result in lower ee. With S-nucleophiles problems with the stability of the nucleophile were encountered.

palladium - catalysis - enantioselective - microwave - phosphine - allylation - ligands

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