Highly Enantioselective Titanium-Catalyzed Cyanation of Imines at Room Temperature
Abdul Majeed Seayad*, Balamurugan Ramalingam, Kazuhiko Yoshinaga, Takushi Nagata and Christina L. L. Chai*
*Institute of Chemical and Engineering Sciences, 1 Pesek Road, Singapore 627833, and Mitsui Chemicals Asia Pacific Ltd., 1 Pesek Road, Singapore 627833, Email: abdul_seayadices.a-star.edu.sg, christina_chaiices.a-star.edu.sg
A. M. Seayad, B. Ramalingam, K. Yushinaga, T. Nagata, C. L. L. Chai, Org. Lett., 2010, 12, 264-267.
DOI: 10.1021/ol902540h (free Supporting Information)
A highly enantioselective cyanation of imines at room temperature in the presence of 5 mol% of a partially hydrolyzed titanium alkoxide (PHTA) precatalyst together with a readily available N-salicyl-β-aminoalcohol ligand gives aminonitriles with up to 98% ee and quantitative yields in 15 min of reaction time. Various N-protecting groups are tolerated.
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