Asymmetric synthesis of (R)- and (S)-4-(substituted benzyl)dihydrofuran-2(3H)-ones: an application of the ruthenium-binap complex-catalysed asymmetric hydrogenation of alkylidenesuccinic acids
作者:Liming Shao、Shiro Miyata、Hitoshi Muramatsu、Hiroyuki Kawano、Youichi Ishii、Masahiko Saburi、Yasuzo Uchida
DOI:10.1039/p19900001441
日期:——
A concise synthesis of (S)- or (R)-4-(substituted benzyl)dihydrofuran-2(3H)-ones (1) with high enantiomeric purity is presented. (S)- or (R)-(Substituted benzyl)succinic acids (6) 97% enantiomeric excess) were first prepared by Ru2Cl4[(R)- or (S)-binap)]2(NEt3) catalysed asymmetric hydrogenation of (substituted benzylidene)succinic acids. The diacids (6) were converted into (R)- or (S)-2-(substituted
提出了具有高对映体纯度的(S)-或(R)-4-(取代的苄基)二氢呋喃-2(3 H)-ones(1)的简明合成方法。首先通过Ru 2 Cl 4 [(R)-或(S)-binap)] 2(NEt 3)催化制备(S)-或(R)-(取代的苄基)琥珀酸(6),对映体过量97%)。 (取代的亚苄基)琥珀酸的不对称氢化。将二酸(6)转化为(R)-或(S)-2-(取代的苄基)丁烷-1,4-二醇(9)和随后的RuH 2(PPh 3)4催化的(9)脱氢内酯化反应,得到内酯(1),其手性构型完全保留中心。