期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 138, 期 36, 页码 11970-11978出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b07382
关键词
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资金
- Spanish Ministerio de Economia y Competitividad (MINECO) [CTQ-2014-57661-R, CTQ2014-60419-R]
- Severo Ochoa Excellence Accreditation [SEV-2013-0319]
- RedINTECAT [CTQ2014-52974-REDC]
- Cellex foundation
- ICREA Funding Source: Custom
Significant progress has been observed in recent years in the synthesis of allylic amines, which are important building blocks, in synthetic chemistry. Most of these processes are effective toward the preparation of allylic amines, with limited potential to introduce three or four different substituents on the olefinic unit in a stereocontrolled fashion. Therefore, the discovery of a mild. and operationally simple protocol allowing such challenging stereoselective synthesis of multisubstituted allylic amines remains an inspiring target. Herein, we report the first general and practical methodology for the stereoselective synthesis of tri- and tetrasubstituted allylic amines based on Pd-catalyzed conversion of allyl surrogates readily obtained from cyclic vinyl carbonates. These rare conversions ate characterized by excellent stereoselectivity, operational Simplicity, mild reaction conditions, and wide scope in reaction partners. DFT studies Were performed to rationalize the stereocontrol in these allylic amine formation reactions, and evidence is provided that the formation of a six-membered palladacyclic intermediate leads toward the formation of (Z)-configured allylic amine products.
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