期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 34, 页码 9839-9843出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201502894
关键词
acylation; amides; IR spectroscopy; ketones; synthetic methods
资金
- National Science Foundation
- McNair Scholars program
- CAREER Award from the National Science Foundation [0643264]
- Direct For Mathematical & Physical Scien [0643264] Funding Source: National Science Foundation
- Division Of Chemistry [0643264] Funding Source: National Science Foundation
A one-pot procedure for the synthesis of unsymmetrical ketones utilizing a pyrrole-bearing carbonyl linchpin reagent (carbonyl linchpin N,O-dimethylhydroxylamine pyrrole; CLAmP) is reported. In contrast to other carbonyl dielectrophile equivalents, CLAmP enables the synthesis of ketones from a variety of organolithium and Grignard reagents. The electrophilic nature of CLAmP enables the addition of less reactive as well as thermally unstable nucleophiles. CLAmP was designed to form kinetically stable tetrahedral intermediates upon the addition of organometallic nucleophiles. Evidence for the existence of persistent tetrahedral intermediates was obtained through in situ IR studies.
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