One-carbon chain extension of esters to α-chloroketones: a safer route without diazomethane

D Wang, MD Schwinden, L Radesca…

文献索引：Wang, Dengjin; Schwinden, Mark D.; Radesca, Lilian; Patel, Bharat; Kronenthal, David; Huang, Ming-Hsing; Nugent, William A. Journal of Organic Chemistry, 2004 , vol. 69, # 5 p. 1629 - 1633

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被引用次数: 41

摘要

The reaction of a variety of methyl esters with dimethylsulfoxonium methylide at 0-25° C affords the chain-extended β-keto dimethylsulfoxonium ylides. Subsequent treatment with hydrogen chloride in THF proceeds with loss of DMSO to afford the corresponding α- chloroketones. This sequence has been utilized to convert the methyl esters of CBZ- protected alanine and valine to the anti N-protected α-amino epoxides, which are ...