Asymmetric synthesis of β-hydroxy-α-alkylamino acids by asymmetric aldol reaction of α-isocyanocarboxylates catalyzed by chiral ferrocenylphosphine-gold(I) complexes
作者:Yoshihiko Ito、Masaya Sawamura、Eiji Shirakawa、Keiichi Hayashizaki、Tamio Hayashi
DOI:10.1016/s0040-4020(01)86034-8
日期:1988.1
Aldol reaction of methyl α-isocyanocarboxylates (CNCH(R)COOMe: R = H, Me, Et, i-Pr) with benzaldehyde or acetaldehyde in the presence of 0.5–1.0 mol% of a chiral (aminoalkyl)ferrocenylphosphine-gold(I) complex gave optically active 4-methoxycarbonyl-4,5-dialkyl-2-oxazolines with high enantioselectivity in a quantitative yield. The oxazolines were converted into optically active β-hydroxy-α-alkylamino
α-异氰基羧酸甲酯(CNCH(R)COOMe:R = H,Me,Et,i-Pr)与苯甲醛或乙醛在0.5–1.0 mol%手性(氨基烷基)二茂铁基膦金(I )配合物以定量收率得到具有高对映选择性的旋光的4-甲氧基羰基-4,5-二烷基-2-恶唑啉。恶唑啉被转化成旋光的β-羟基-α-烷基氨基酸甲酯。