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Volumn 70, Issue 4, 2005, Pages 1505-1507

Cycloisomerization of 1,6-enynes using acetate as a nucleophile under palladium (II) catalysis

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ISOMERIZATION; PALLADIUM COMPOUNDS; QUENCHING; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 13844320897     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048414o     Document Type: Article
Times cited : (67)

References (24)
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    • note
    • Ratio of compounds 1:2 (or 2:1) is calculated according to the signal intensity of the NMR spectra of the mixture, which is inseparable on the silica gel column chromatography, and we did not assign the spectral signal specifically to 1 and 2.
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    • note
    • 1H NMR experiment as shown here. (Chemical Equation Presented)
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    • note
    • Ee of 8a was determined by chiral HPLC using the Chiralcel AD column eluting with 9:1 hexane/2-propanol (λ = 214 nm). Absolute stereochemistry of the chiral center in product 8a has not been determined.
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    • For recent contributions to enantioselective enyne cyclizations, see: (a) Hatano, M.; Mikami, K. J. Am. Chem. Soc. 2003, 125, 4704. (b) Chakrapani, H.; Liu, C.; Widenhoefer, R. A. Org. Lett. 2003, 5, 157. (c) Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526. (d) Cao, P.; Zhang, X. Angew. Chem., Int. Ed. 2000, 39, 4104.
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    • For recent contributions to enantioselective enyne cyclizations, see: (a) Hatano, M.; Mikami, K. J. Am. Chem. Soc. 2003, 125, 4704. (b) Chakrapani, H.; Liu, C.; Widenhoefer, R. A. Org. Lett. 2003, 5, 157. (c) Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526. (d) Cao, P.; Zhang, X. Angew. Chem., Int. Ed. 2000, 39, 4104.
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    • For recent contributions to enantioselective enyne cyclizations, see: (a) Hatano, M.; Mikami, K. J. Am. Chem. Soc. 2003, 125, 4704. (b) Chakrapani, H.; Liu, C.; Widenhoefer, R. A. Org. Lett. 2003, 5, 157. (c) Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526. (d) Cao, P.; Zhang, X. Angew. Chem., Int. Ed. 2000, 39, 4104.
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