Influences of catalyst configuration and catalyst loading on selectivities in reactions of diazoacetamides. Barrier to equilibrium between diastereomeric conformations

Organic Letters

Volumn 5, Issue 4, 2003, Pages 407-410

  Doyle, Michael P ^a   Hu, Wenhao ^a   Wee, Andrew G H ^b   Wang, Zhongyi ^b   Duncan, Sammy C ^b  

^a University of Arizona   (United States)

^b UNIVERSITY OF REGINA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; CARBON; HYDROGEN; METHYL GROUP; DIAZOACETAMIDE; DIAZONIUM COMPOUND;

ARTICLE; CATALYST; CONFORMATIONAL TRANSITION; DIASTEREOISOMER; ENANTIOMER; STEREOISOMERISM; CATALYSIS; CHEMISTRY;

CATALYSIS; DIAZONIUM COMPOUNDS; STEREOISOMERISM;

EID: 0037669301     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027157b     Document Type: Article

References (20)

1. Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
2. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley: New York, 1998.
3. Davies, H. M. L.; Antoulinakis, E. G. Org. React. (NY) 2001, 57, 1.
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15. 2: % yield = 75; 9:10:11 = 9:16:75; % ee 9 = 81; % ee 11 = 34.
16. 2Cl: % yield = 74; 9:10:11 = 19:15: 66; % ee 9 = 75; % ee 11 = 7.
17. The same principles apply to enantioselection in aromatic cycloaddition. This report is only the second to document enantioselectivity for aromatic cycloaddition of diazoacetamides and diazoacetates: Doyle, M. P.; Ene, D. G.; Forbes, D. C.; Pillow, T. H. J. Chem. Soc., Chem. Commun. 1999, 1691.
18. Wee, A. G. H.; Duncan, S. C. Tetrahedron Lett. 2002, 43, 6173.
19. Takahata, H.; Banba, Y.; Tajima, M.; Momose, T. J. Org Chem. 1991, 56, 240.
20. 4 via ligand exchange.