The effect of substituents of α-alkyl sidechains on furan-diazoester interactions

Tetrahedron Letters

Volumn 40, Issue 30, 1999, Pages 5439-5442

  Wenkert, Ernest ^a   Khatuya, Haripada ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

Acetals; Carbenes and carbenoids; Diazo compounds; Furans

Indexed keywords

ACETAL; ALKYL GROUP; ESTER DERIVATIVE; FURAN DERIVATIVE;

ACETYLATION; ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0033165870     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01062-X     Document Type: Article

References (19)

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8. (b) After iodine-isomerization, the crude material was treated with DMAP in EtOH at rt for 8 h.
9. 2O), 128.8 (C-2), 135.3 (C-5), 138.1 (C-4), 141.3 (C-3), 165.8 (C-1), 200.1 (C-6).
10. (a) For similar 2:1 adducts with aryl aldehydes, see Alt, M.; Mass, G. Tetrahedron 1994, 50, 7435 and Doyle, M. P.; Forbes, D. C.; Protopova, M. N.; Stanley, S. A.; Vasbinder, M. M.; Xavier, K. R. J. Org. Chem. 1997, 62, 7210.
11. (a) For similar 2:1 adducts with aryl aldehydes, see Alt, M.; Mass, G. Tetrahedron 1994, 50, 7435 and Doyle, M. P.; Forbes, D. C.; Protopova, M. N.; Stanley, S. A.; Vasbinder, M. M.; Xavier, K. R. J. Org. Chem. 1997, 62, 7210.
12. (b) The relative trans- stereochemistry of the 1,2-disubstituents also was supported by the following experiment: When the acetal mixture was treated with NaOEt in EtOH, the ratio remained unchanged.
13. 2CO), 82.4 (C-2'), 107.2 (C-4), 111.1 (C-3), 142.4 (C-5), 146.3 (C-2), 151.3 (C-1'), 168.3 (C=O). For similar reactions with saturated ketones, see Lottes, A. C.; Landgrebe, J. A.; Larsen, K. Tetrahedron Lett. 1989, 30, 4089.
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16. 2O-light petroleum ether).
17. 2s), 104.4 (C-7), 107.1 (C-6), 127.3 (C-5), 129.0 (C-2), 135.3 (C-4), 136.8 (C-3), 168.6 (C=O).
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