期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 67, 期 7, 页码 2309-2314出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo011139a
关键词
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The development of a highly efficient and stereoselective methodology for the preparation of alpha-amino acids is described. The chiral template, tricyclic iminolactone 7, was synthesized from (1R)-(+)camphor in five steps in 50% overall yield. Alkylation of iminolactone 7 afforded the CL-monosubstituted products in good yields (74-96%) and excellent diastereoselectivities (>98%). Hydrolysis of the alkylated iminolactones furnished the desired alpha-amino acids in good yields and enantioselectivities with nearly quantitative recovery of the chiral auxiliary 4.
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