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

作者：Canipa Steven J; Stute Annika; O' Brien Peter

来源：Tetrahedron, 2014, 70(40): 7395-7403.

DOI：10.1016/j.tet.2014.06.117

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

Four new copper(II)/diamine complexes comprising some (+)-sparteine surrogates and a cyclohexanederived 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.

• 出版日期2014-10-7