4‐l‐menthyloxycarbonyl 5‐aryl prolinates were studied as organocatalysts of a novel three‐component reaction of cyclohexanone, benzoic acid, and β‐nitrostyrene. The presence of ortho‐halogen atom in 5‐aryl fragment of the catalyst is favored for driving the formation of chiral 7a‐hydroxyoctahydro‐2H‐indol‐2‐one scaffold. 5‐(o‐Chlorophenyl) prolinate selectively afforded 3‐phenyl‐7a‐hydroxyoctahydro‐2H‐indol‐2‐one with ee 63%, whereas 5‐phenyl prolinate led to conjugation of β‐nitrostyrene to cyclohexanone (the Michael adduct). Plausible chlorine effect is accounted for the specific interaction of the 5‐aryl prolinate enamine intermediate with β‐nitrostyrene in the transition state.

中文翻译：

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丙酸5-芳基酯的有机催化下环己酮，β-硝基苯乙烯和苯甲酸之间不对称相互作用的化学选择性问题。

4-升-menthyloxycarbonyl 5-芳prolinates进行了研究如环己酮，苯甲酸，和β硝基苯乙烯的一种新颖的三组分反应的有机催化剂。催化剂5-芳基片段中存在邻卤素原子有助于推动手性7a-羟基八氢-2 H-吲哚-2-酮骨架的形成。脯氨酸5-（邻-氯苯基）选择性提供ee 63％的3-苯基-7a-羟基八氢-2 H-吲哚-2-酮，而脯氨酸5-苯基导致β-硝基苯乙烯与环己酮结合（迈克尔加合物） 。可能的氯作用是过渡态的5-芳基脯氨酸脯氨酸烯胺中间体与β-硝基苯乙烯之间特定相互作用的原因。