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Volumn 4, Issue 22, 2002, Pages 3887-3890

Enantio- and Diastereoselective Synthesis of cis-2-Aryl-3-methoxycarbonyl-2,3-dihydrobenzofurans via the Rh(II)-Catalyzed C-H Insertion Process

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ARTICLE;

EID: 0012630744     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0267127     Document Type: Article
Times cited : (153)

References (47)
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    • 4-catalyzed C-H insertion in a related system, where reactions in hexanes at -50°C took 72 h for completion. In their work, the enantioselectivity up to 94% ee was obtained for insertion into methine C-H bonds, whereas C-H insertion into a methylene group produced a mixture of cis-and trans-dihydrobenzofurans with up to 63% ee of the cis isomer. See: Davies, H. M. L.; Grazini, M. V. A.; Aouad, E. Org. Lett. 2001, 3, 1475.
    • (2001) Org. Lett. , vol.3 , pp. 1475
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    • Very recently, Nakamura and co-workers have reported a mechanism of dirhodium(II) tetracarboxylate-catalyzed C-H insertion reactions based on a detailed computational analysis. See: Nakamura, E.; Yoshikai, N.; Yamanaka, M. J. Am. Chem. Soc. 2002, 124, 7181.
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    • note
    • 4, toluene, -78 °C or room temperature].


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