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Volumn 72, Issue 22, 2007, Pages 8459-8471

Organocatalytic asymmetric Robinson annulation of α,β- unsaturated aldehydes: Applications to the total synthesis of (+)-palitantin

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLALDEHYDES; PALITANTIN; ROBINSON ANNULATION;

EID: 35548940800     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701477v     Document Type: Article
Times cited : (110)

References (141)
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    • Individual exposure to L-Pro of 1a or 2a gave the corresponding self-[4 + 2]- and self-[3 + 3]-cycloaddition adducts, respectively. However, in the reaction of the mixture of 1a, 2a, and L-Pro, cross-[4 + 2]-cycloaddition was dominant and less than 5% yields of the self-condensation adducts were observed.
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    • The same hypothesis for the self-condensation of other α,β-unsaturated aldehydes was supported independently by NMR and mass spectrometry; see ref 16b.
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    • 13C spectra of 17 were identical to the spectra in the literature. See: Angelaud, R.; Babot, O.; Charvat, T.; Landais, Y. J. Org. Chem. 1999, 64, 9613 and supporting information.
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