A New Strategy for the Synthesis of α-Difluoromethyl-Substituted α-Hydroxy and α-Amino Acids

…, N Sewald, T Michel, AF Kolomiets…

文献索引：Osipov, Sergey N.; Golubev, Alexander S.; Sewald, Norbert; Michel, Thomas; Kolomiets, Alexey F.; Fokin, Alexander V.; Burger, Klaus Journal of Organic Chemistry, 1996 , vol. 61, # 21 p. 7521 - 7528

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被引用次数: 73

摘要

A new method for the preparation of α-chlorodifluoromethyl-, α-bromodifluoromethyl-, and α- difluoromethyl-substituted α-hydroxy and α-amino acid esters 11, 19-21 is described. The key step of the synthesis is the regioselective alkylation of ketones 5, 7-9 and imines 16-18 with C-nucleophiles. The ketones 7-9 are readily available from 3, 3, 3-trifluorolactate 1 by a five-step procedure. Subsequent removal of the protecting groups from 19-21 provides the ...