ol051423e_si_001.pdf (200.13 kB)

Cu(I)-Catalyzed Direct Enantioselective Cross Aldol-Type Reaction of Acetonitrile

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journal contribution
posted on 18.08.2005, 00:00 by Yutaka Suto, Riichiro Tsuji, Motomu Kanai, Masakatsu Shibasaki
Direct catalytic enantioselective cross aldol-type reaction of an acetate surrogate was developed using Cu alkoxide−chiral phosphine complexes as catalysts. Chemoselective activation and deprotonation of the donor substrate (acetonitrile) by the soft metal alkoxide in a strongly donating solvent (HMPA) are key to success in this reaction. Useful chemical yields and promising enantioselectivities are produced using either DTBM-SEGPHOS or a tuned BIPHEP as a chiral ligand.