Lewis acid-catalyzed reactions of ethyl diazoacetate with aldehydes.: Synthesis of α-formyl esters by a sequence of aldol reaction and 1,2-nucleophilic rearrangement
Lewis acid-catalyzed reactions of ethyl diazoacetate with aldehydes.: Synthesis of α-formyl esters by a sequence of aldol reaction and 1,2-nucleophilic rearrangement
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DOI：
10.1016/s0040-4039(99)00932-6
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发表时间：
1999-07-02
影响因子：
1.8
通讯作者：
Wada, E
中科院分区：
文献类型：
--
作者：
Kanemasa, S;Kanai, T;Wada, E
重氮乙酸乙酯与各种醛在刘易斯酸催化剂存在下反应，生成β-酮酯或α-甲酰基酯，产物的类型主要取决于所用刘易斯酸催化剂的性质。由刘易斯酸如SnCl 2和SnCl 4催化的反应通过亲核1，2-氢化物迁移提供β-酮酯，而由三甲基甲硅烷基三氟甲磺酸酯催化的那些通过醛的取代基的迁移得到α-甲酰基酯。讨论了反应机理。(C)1999 Elsevier Science Ltd.版权所有。
Ethyl diazoacetate reacts with a variety of aldehydes in the presence of a Lewis acid catalyst to give either beta-keto esters or alpha-formyl esters, the types of products mainly depending upon the nature of Lewis acid catalysts employed. Reactions catalyzed by Lewis acids such as SnCl2 and SnCl4 provide beta-keto esters via nucleophilic 1,2-hydride migration, while those catalyzed by trimethylsilyl triflate give alpha-formyl esters via migration of the substituent of the aldehyde. Reaction mechanisms are discussed. (C) 1999 Elsevier Science Ltd. All right reserved.