Issue 9, 1989

Diastereofacial selection in the conjugate reduction of γ-alkyl-α,β-unsaturated carbonyl derivatives. Stereocontrol dictated by aromatic ring–Pd interaction

Abstract

Conjugate reduction of the ethylidene-malonate (1a) and -malonitrile (1b) bearing the chiral centre at the γ-position with hydride reagents or with Li–NH3 gives the anti-isomer (2) preferentially, while the hydrogenation with Pd–C produces the syn-isomer (3) predominantly: the syn-preference is due to a strong interaction between the aromatic π-system and palladium metal.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1989, 1703-1705

Diastereofacial selection in the conjugate reduction of γ-alkyl-α,β-unsaturated carbonyl derivatives. Stereocontrol dictated by aromatic ring–Pd interaction

Y. Yamamoto, S. Nishii and T. Ibukab, J. Chem. Soc., Perkin Trans. 1, 1989, 1703 DOI: 10.1039/P19890001703

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