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Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to β-Nitroolefins: Formal Synthesis of (S)-SKF 38393

Kung-Chih Huang, Balraj Gopula, Ting-Shen Kuo, Chien-Wei Chiang, Ping-Yu Wu, Julian P. Henschke and Hsyueh-Liang Wu*

*Department of Chemistry and Instrumentation Center, Department of Chemistry, National Taiwan Normal University, No. 88, Section 4, Tingzhou Road Taipei 11677, Taiwan, Republic of China, Email: hlwntnu.edu.tw

K.-C. Huang, B. Gopula, T.-S. Kuo, C.-W. Chiang, P.-Y. Wu, J. P. Henschke, Hsyueh-Liang Wu, Org. Lett., 2013, 15, 5730-5733.

DOI: 10.1021/ol4027599 (free Supporting Information)


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Abstract

An efficient enantioselective addition of an array of arylboronic acids to various β-nitrostyrenes is catalyzed by a novel and reactive rhodium-diene catalyst and provides β,β-diarylnitroethanes in very good yields with excellent enantioselectivities. Additions to 2-heteroarylnitroolefins and 2-cycloalkylnitroolefins similarly provide the desired products with high enantioselectivities and yields.

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Key Words

arylation, nitro compounds


ID: J54-Y2013