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Rhodium-Catalyzed Asymmetric Arylation of Allyl Sulfones under the Conditions of Isomerization into Alkenyl Sulfones

Kelvin Meng-Hui Lim and Tamio Hayashi*

*Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore, Email: tamiohimre.a-star.edu.sg

K. M.-H. Lim, T. Hayashi, J. Am. Chem. Soc., 2015, 137, 3201-3204.

DOI: 10.1021/jacs.5b00216 (free Supporting Information)


Abstract

The reaction of 3-sulfolene with arylboronic acids in the presence of a chiral diene-rhodium catalyst under highly basic conditions gave high yields of 3-arylsulfolanes with high enantioselectivity via a base-catalyzed isomerization to the more reactive 2-sulfolene.

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Effect of Chiral Diene Ligands in Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to α,β-Unsaturated Sulfonyl Compounds

T. Nishimura, Y. Takiguchi, T. Hayashi, J. Am. Chem. Soc., 2012, 134, 9086-9089.


Key Words

S-heterocycles, arylation


ID: J48-Y2015