Efficient two-step conversion of α,β-unsaturated aldehydes to optically active γ-oxy-α,β-unsaturated nitriles and its application to the total synthesis of (+)-patulolide C

Organic Letters

Volumn 5, Issue 17, 2003, Pages 3021-3024

  Tian, Jun ^a   Yamagiwa, Noriyuki ^a   Matsunaga, Shigeki ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CHEMICAL COMPOUND; LEWIS ACID; NITRILE; PATULOLIDE C; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYANATION; ENANTIOSELECTIVITY; ETHOXYCARBONYLATION; SYNTHESIS;

EID: 0141744527     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034944f     Document Type: Article

References (31)

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30. Selectivity in the reduction of 7 with (S)-CBS was C11-R/S = 86/14 (72% ee), which was calculated from dr and ee value of 10. In the model study using 2-octanone and 30 mol % of (S)-CBS, 2-octanol was obtained in 75% ee at -78 °C after 20 h. The calculated ee value for the reduction of 7 (72% ee) matched well with that in the model study. For detailed calculations and discussion of statistical asymmetric amplification, see the Supporting Information. For a recent application of statistical asymmetric amplification in the total synthesis, see: (a) Huo, S.; Negishi, E. Org. Lett. 2001, 3, 3253 and references therein. For a leading reference, see: (b) Vigneron, J. P.; Dhaenens, M.; Horeau, A. Tetrahedron 1973, 29, 1055.
31. Selectivity in the reduction of 7 with (S)-CBS was C11-R/S = 86/14 (72% ee), which was calculated from dr and ee value of 10. In the model study using 2-octanone and 30 mol % of (S)-CBS, 2-octanol was obtained in 75% ee at -78 °C after 20 h. The calculated ee value for the reduction of 7 (72% ee) matched well with that in the model study. For detailed calculations and discussion of statistical asymmetric amplification, see the Supporting Information. For a recent application of statistical asymmetric amplification in the total synthesis, see: (a) Huo, S.; Negishi, E. Org. Lett. 2001, 3, 3253 and references therein. For a leading reference, see: (b) Vigneron, J. P.; Dhaenens, M.; Horeau, A. Tetrahedron 1973, 29, 1055.