Synthesis p. 127 - 131 (1992)
Update date:2022-08-04
Topics:
Swiss
Hinkley
Maryanoff
Liotta
Complementary facial selectivity can be achieved in conjugate additions to γ-hydroxyenones by using either Grignard reagents or cuprates. In the case of the former, preliminary complexation of the magnesium reagent with the resident alkoxide, followed by alkyl group transfer, results in the exclusive formation of the syn product. Conversely, cuprate conjugate additions proceed in an anti fashion, presumably because, in this mode of addition, coulombic repulsions are minimized.
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(1966)
