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Use of copper(II)/diamine catalysts in the desymmetrisation of meso-diols and asymmetric Henry reactions: Comparison of (-)-sparteine and (+)-sparteine surrogates

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JournalTetrahedron
DatePublished - Oct 2014
Issue number40
Volume70
Number of pages9
Pages (from-to)7395-7403
Original languageEnglish

Abstract

Four new copper(II)/diamine complexes comprising some (+)-sparteine surrogates and a cyclohexane-derived diamine were prepared and evaluated as chiral catalysts in desymmetrisation of . meso-diols and asymmetric Henry reactions. Mono-benzoylation reactions generated two products with high enantioselectivity (90:10 to 97:3 er). Asymmetric Henry reactions gave nitro alcohols in 90:10 to 98:2 er. Notably, the sense of induction with the (+)-sparteine surrogates was opposite to that obtained using the copper(II)/(-)-sparteine complex. One of the nitro alcohol products was utilised in a concise synthesis of a chiral morpholine.

    Research areas

  • Benzoylation, Copper(II) complexes, Diamines, Henry reaction, Morpholine

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