Featured Article pubs.acs.org/joc
Rhodium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Nitroalkenes Using Olefin−Sulfoxide Ligands Feng Xue, Dongping Wang, Xincheng Li, and Boshun Wan* Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China S Supporting Information *
ABSTRACT: An efficient rhodium/olefin−sulfoxide catalyzed asymmetric conjugate addition of organoboronic acids to a variety of nitroalkenes has been developed, where 2-methoxy-1-naphthyl sulfinyl functionalized olefin ligands have shown to be highly effective and are applicable to a broad scope of aryl, alkyl, and heteroaryl nitroalkenes.
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INTRODUCTION Over the past few years, the Rh-catalyzed enantioselective conjugate addition of organoboron reagents to electron deficient olefins has been established as a powerful and straightforward method for the construction of new carbon−carbon bonds and has become increasingly explored.1 Although many exciting results have been achieved in the asymmetric addition to α,β-unsaturated carbonyl compounds2 and related aldimines,3 there were few reports with respect to nitroalkenes,4,5 likely because of the challenge in control of the reaction stereoselectivity. Since Hayashi’s pioneering work was reported in the asymmetric addition to cyclic nitroalkenes using a rhodium/binap (Figure 1, 1) catalyst in 2000,4a little progress has been made in the reaction of cyclic nitroalkenes,4b,c and related examples focusing on 2-nitrostyrenes were only reported with low levels of enantioselectivities (
