未活化直链1,3 - 二烯的不对称氢乙烯基化反应
Asymmetric hydrovinylation of unactivated linear 1,3-dienes.
作者信息
Sharma Rakesh K, RajanBabu T V
机构信息
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.
出版信息
J Am Chem Soc. 2010 Mar 17;132(10):3295-7. doi: 10.1021/ja1004703.
Abstract
Monosubstituted acyclic (E)-1,3-dienes undergo efficient hydrovinylation giving (Z)-3-alkylhexa-1,4-dienes upon treatment with catalytic amounts of bidentate phosphine-CoCl(2) complexes {P~P} and Me(3)Al in an atmosphere of ethylene. The regioselectivity of the reaction (i.e., 1,4- or 1,2-addition) depends on the nature of the ligand and temperature at which the reaction is carried out. Complexes derived from (RR)-DIOP and (SS)-BDDP at -45 degrees C give very high enantioselectivities for several prototypical 1,3-dienes. In sharp contrast to the corresponding Ni(II)-catalyzed hydrovinylation, 1-aryl-substituted 1,3-dienes give almost exclusively achiral linear 1,4-addition products, unless the 2-position is also substituted. Solid-state structures of the precatalysts are presented.
摘要
单取代无环（E）-1,3-二烯在乙烯气氛中，用催化量的双齿膦 - CoCl₂配合物{P~P}和Me₃Al处理时，能高效地进行氢乙烯基化反应，生成（Z）-3-烷基己-1,4-二烯。反应的区域选择性（即1,4-或1,2-加成）取决于配体的性质以及反应进行时的温度。在-45℃下，由（RR）-DIOP和（SS）-BDDP衍生的配合物对几种典型的1,3-二烯具有非常高的对映选择性。与相应的Ni（II）催化的氢乙烯基化反应形成鲜明对比的是，1-芳基取代的1,3-二烯几乎只生成非手性的线性1,4-加成产物，除非2-位也被取代。文中给出了前催化剂的固态结构。
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