Journal of the American Chemical Society p. 7890 - 7892 (2010)
Update date:2022-08-02
Topics:
Poisson, Thomas
Yamashita, Yasuhiro
Kobayashi, Shu
Catalytic asymmetric protonation of chiral calcium enolates was performed. Chiral calcium enolates, prepared in situ from imides and malonates via 1,4-addition in the presence of catalytic amounts of Ca(OEt)2, Ph-PyBox, and achiral phenol, were smoothly protonated to afford adducts bearing tertiary asymmetric carbons in high yields with high enantioselectivities. The adducts were readily converted to optically active 2-substituted 1,5-dicarboxylic acid derivatives.
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