联二芳基轴手性有机小分子催化合成氧化吲哚类螺环化合物
Synthesis of spirooxindoles catalyzed by biaryl axiallyl chiral organic small molecules
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摘要: 由(R)-2,2′-二羟基-1,1′-联二萘-3,3′-二羧酸与手性胺反应合成轴手性联二萘酚酰胺类的有机催化剂( 1a ~ 1d ),将其用于催化合成螺双烯酮-羟吲哚的反应. 实验结果表明:在40 ℃下,以二氯甲烷为溶剂,x=20% 1d 作为催化剂,合成的螺环化合物获得较好的收率(93%)和较高的对映选择性(91%).Abstract: Organic catalysts of the axial chiral binaphtholamides( 1a ~ 1d ) were synthesized by reaction of (R)-2, 2′-dihydroxy-1, 1′-binaphthalene-3, 3′-dicarboxylic acid and chiral amines. It was used to catalyze asymmetric reaction of diketene with oxindole.The reaction was performed in the presence of 20%(x) at 40 °C in CH2Cl2, spirooxindoles can be obtained with higher yield (up to 93%) and better enantioselectivities(up to 91% ee).