Pure Appl. Chem., 2005, Vol. 77, No. 12, pp. 2105-2110
doi:10.1351/pac200577122105
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.
Keywords: aza-Baylis-Hillman; Baylis-Hillman reaction; chiral phosphine Lewis bases; methyl vinyl ketone; N-sulfonated imines.
*Paper based on a presentation at the 7th IUPAC International Conference on Heteroatom Chemistry (ICHAC-7), Shanghai, China, 21-25 August 2004. Other presentations are published in this issue, pp. 1985-2132.