Four hydroxyls are better than two. The use of a chiral lithium salt of 3,3 '-bis-methanol-2,2 '-binaphthol as a multifunctional catalyst of enantioselective Michael addition reactions

作者：Belokon Yuri N^*; Gugkaeva Zalina T; Maleev Victor I; Moskalenko Margarita A; Tsaloev Alan T; Khrustalev Victor N; Hakobyan Karine V

来源：Tetrahedron: Asymmetry , 2011, 22(2): 167-172.

DOI：10.1016/j.tetasy.2010.12.003

The catalytic performance of the Li salt of (S)- or (R)-3,3'-bis[bis-(phenyl)hydroxymethyl]-2,2'-dihydroxy-dinaphthalene-1,1' (BIMBOL) in asymmetric Michael additions of malonic acid derivatives and toluedine has been studied. Nitrostyrene and cyclohex-2-enone were chosen as Michael acceptors. Efficient asymmetric C-C and C-N bond formations with ee's of up to 95% at room temperature were observed. A transition state model of the malonic ester addition to cyclohex-2-enone has been proposed based on the molecular structure of the acetone solvate of BIMBOL. The impact of the catalyst self-association on its performance is also discussed.

• 出版日期2011-1-31