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Pure Appl. Chem., 2005, Vol. 77, No. 12, pp. 2105-2110

Chiral phosphine Lewis bases in catalytic, asymmetric aza-Morita-Baylis-Hillman reaction

Min Shi and Lian-Hui Chen

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China

Abstract: In the aza-Morita-Baylis-Hillman reaction of N-sulfonated imines with methyl vinyl ketone (MVK) promoted by chiral phosphine Lewis base: (R)-2'-diphenylphosphanyl-[1,1']binaphthalenyl-2-ol (LB1) (10 mol %), the aza-Morita-Baylis-Hillman adducts were obtained in good yields with high ee (70-94 % ee) at -30 °C in THF. The scope and limitations of this reaction have been disclosed.