1033076-48-0Relevant academic research and scientific papers
Diastereo- and enantioselective construction of γ-butenolides through chiral phosphane-catalyzed allylic alkylation of morita-baylis-hillman acetates
Wei, Yin,Ma, Guang-Ning,Shi, Min
supporting information; experimental part, p. 5146 - 5155 (2011/10/12)
A series of multifunctional, chiral amide-phosphane organocatalysts have been designed and synthesized for the allylic substitution of Morita-Baylis-Hillman (MBH) acetate with 2-trimethylsilyloxyfuran for butenolide synthesis. This reaction was achieved in good to excellent yield (42-98%) and high ee (85-99%) with respect to a wide range of substrates in absolute MeOH or CH3CN, using chiral amide-phosphane organocatalysts with an amide moiety including an active proton. NMR tracing experiments identified the critical phosphonium intermediates involved in the catalytic cycles. Computational studies disclosed the origins of diastereo- and enantioselectivity, in particular, revealing that the active proton of the amide moiety is the critical factor for the catalyst to have high enantiofacial control. The diastereo- and enantioselective construction of γ-butenolides was developed through allylic alkylation of Morita-Baylis-Hillman acetates catalyzed by chiral amide-phosphanes, affording the corresponding products in good yield (42-98%) and high ee (85-99%) with a wide range of substrates. The reaction mechanism was investigated by NMR tracing experiments and computational studies. Copyright
Chiral phosphine-catalyzed enantioselective construction of γ-butenolides through substitution of morita-baylis-hillman acetates with 2-trimethylsilyloxy furan
Jiang, Ying-Qing,Shi, Yong-Ling,Shi, Min
, p. 7202 - 7203 (2008/12/21)
Chiral multifunctional phosphine (R)-N-(2′-diphenylphosphanyl-[1,1-]binaphthalenyl-2-yl)methanesulfonamide L2 or (R)-N-(2′-diphenylphosphanyl-[1,1-]binaphthalenyl-2-yl)acetamide L3 is an efficient catalyst in the allylic substitutions of MBH acetates 1 with 2-trimethylsilyloxy furan 2 to provide γ-butenolides 3 in good to excellent yields and enantiomeric excesses in the presence of water. Copyright
