Trifluoromethylated amino alcohol as chiral auxiliary for highly diastereoselective and fast Simmons–Smith cyclopropanation of allylic amine |
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| Institution: | 1. Department of Chemistry, Bishop Moore College, Mavelikara, Alappuzha, Kerala 690110, India;2. Department of Physics, Centre for Advanced Functional Materials, Bishop Moore College, Mavelikara, Alappuzha, Kerala 690110, India;3. Department of Chemistry, BLDEA''s S. B. Arts and K. C. P. Science College, Vijayapur, Karnataka 586103, India;4. Department of Physics, Sri D Devaraj Urs Government First Grade College, Hunsur, Mysore, Karnataka, 571105, India;5. Department of Physics, Yuvaraja College (Constituent College), University of Mysore, Mysore, Karnataka 570005, India;6. Department of Chemistry, Karnatak University''s Karnatak Science College, Dharwad, Karnataka 580001, India |
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| Abstract: | Three advantages of a trifluoromethylated amino alcohol auxiliary in the Simmons–Smith cyclopropanation of allylic amines are described. The trifluoromethylated amino alcohol auxiliary reduces unwanted side reactions induced by its acidic, and thus less nucleophilic, hydroxy group. The auxiliary accelerated the reaction rate by its electron-withdrawing effect, and promoted the reaction with excellent diastereoselectivity. |
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