Enantioselective Intramolecular Oxidative Aminocarbonylation of Alkenylureas Catalyzed by Palladium−Spiro Bis(isoxazoline) Complexes
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- 作者：Tetsuya Tsujihara ; Toshio Shinohara ; Kazuhiro Takenaka ; Shinobu Takizawa ; Kiyotaka Onitsuka ; Minoru Hatanaka ; Hiroaki Sasai
- 刊名：Journal of Organic Chemistry
- 出版年：2009
- 出版时间：December 18, 2009
- 年：2009
- 卷：74
- 期：24
- 页码：9274-9279
- 全文大小：863K
- 年卷期：v.74,no.24(December 18, 2009)
- ISSN：1520-6904
文摘
An enantioselective synthesis of tetrahydropyrrolo[1,2-c]pyrimidine-1,3-diones via a palladium-catalyzed intramolecular oxidative aminocarbonylation is described. The carbon−carbon double bond of alkenylurea substrates has been shown to react intramolecularly with a nitrogen nucleophile in the presence of a palladium catalyst under a carbon monoxide atmosphere. The use of a chiral spiro bis(isoxazoline) ligand (SPRIX) is essential to obtain the desired products in optically active forms. In comparison with the coordination ability of other known ligands, this peculiar character of SPRIX originates from two structural characteristics: low σ-donor ability of the isoxazoline coordination site and rigidity of the spiro skeleton.