20432-97-7Relevant academic research and scientific papers
NovelN-transfer reagent for converting α-amino acid derivatives to α-diazo compounds
Lu, Guan-Han,Huang, Tzu-Chia,Hsueh, Hsiao-Chin,Yang, Shin-Cherng,Cho, Ting-Wei,Chou, Ho-Hsuan
supporting information, p. 4839 - 4842 (2021/05/25)
A novel universalN-transfer reagent for direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of α-substituted-α-diazo carbonyl compounds from α-amino acid derivatives but also permits preparation of α-diazo dipeptides fromN-terminal dipeptides (32 examples, up to 91%).
Direct cycle between co-product and reactant: An approach to improve the atom economy and its application in the synthesis and protection of primary amines
Guan, Qi,Jiang, Mingyang,Wu, Junhui,Zhai, Yanpeng,Wu, Yue,Bao, Kai,Zhang, Weige
supporting information, p. 5794 - 5799 (2016/11/06)
Two important goals of green chemistry are to maximize the efficiency of reactants and to minimize the production of waste. In this study, a novel approach to improve the atom economy of a chemical process was developed by incorporating a direct cycle between a co-product and a reactant of the same reaction. To demonstrate this concept, recoverable 3,4-diphenylmaleic anhydride (1) was designed and used for the atom-economical synthesis of aliphatic primary amines from aqueous ammonia. In each individual cycle, only ammonia and alkyl halide were consumed, and 1 was recovered in nearly a quantitative yield. In this approach for developing atom-economical protecting agents, 1 showed good performance as a recoverable protecting agent for primary amines. The broad substrate scope, good tolerance to various reaction conditions, and high reaction and recovery rates make 1 a valuable complement to conventional primary amine protecting agents.
Selective Reactions of Azide-Substituted α-Diazo Amides with Olefins and Alcohols Using Rhodium(II) Catalysts
Jeganathan, Alwarsamy,Richardson, Steward K.,Mani, Rajarathnam S.,Haley, Boyd E.,Watt, David S.
, p. 5362 - 5367 (2007/10/02)
The synthesis and addition of azide-substituted α-diazo amides such as N-(4-azidophenyl)-α-diazoacetamide and N-(4-azido-2-hydroxyphenyl)-α-diazoacetamide to olefins and alcohols using either rhodium(II) acetate or preferably rhodium(II) pivalate provided cyclopropanecarboxamides and α-alkoxy amides, respectively, without disrupting the azide functionality.These azide-bearing α-diazo amides are potentially useful in the preparation of photoaffinity cross-linking reagents for studying the mechanism of action of natural products.
