1,2-aryl and 1,2-hydride migration in transition metal complex catalyzed diazo decomposition: A novel approach to α-aryl-β-enamino esters

Organic Letters

Volumn 3, Issue 19, 2001, Pages 2989-2991

  Jiang, Nan ^a   Qu, Zhaohui ^a   Wang, Jianbo ^a  

^a Peking University   (China)

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ARTICLE;

EID: 0000467813     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016324p     Document Type: Article

References (29)

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18. 3 (20 mL) was carefully added. Usual workup gave a crude product, which was purified by column chromatography with silica gel.
19. For review, see: Weinreb, S. M. Top. Curr. Chem. 1997, 190, 131. For a recent example, see: Lu, W.; Chan, T. H. J. Org. Chem. 2001, 66, 3467.
20. For review, see: Weinreb, S. M. Top. Curr. Chem. 1997, 190, 131. For a recent example, see: Lu, W.; Chan, T. H. J. Org. Chem. 2001, 66, 3467.
21. The cis isomer has intramolecular hydrogen bonding between N-H and the carbonyl oxygen. The spectra data for all diazo compounds and the α-aryl-β-enamino esters are submitted as Supporting Information.
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23. 4; see ref 2c.
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25. 4 (1 mg) was added. The reaction mixture was stirred at 0°C for 10 min. The solvent was removed under vacuum, and the residue was purified by chromatography or recrystallization.
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27. However, we could not rule out the possibility that migration concerted with rhodium dissociation, as one of the referees suggested.
28. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper Collins Publishers: New York, 1987.
29. Pirrung, M. C.; Morehead, A. T., Jr. J. Am. Chem. Soc. 1994, 116, 8991.