期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 129, 期 24, 页码 7488-+出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja071523a
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资金
- Engineering and Physical Sciences Research Council [GR/S57785/01] Funding Source: researchfish
On lithiation, N-benzyl ureas varying N'-aryl substituents undergo a migration of the aryl ring to the alpha carbon of the N-benzyl group. With chiral, enantiomerically pure N-alpha-methylbenzyl ureas, the rearrangement is stereospecific and creates a new, fully substituted stereogenic center alpha to N. Removal of the urea function by N-nitrosation and hydrolysis allows the synthesis of chiral tertiary carbinamines in high enantiomeric purity.
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