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Volumn , Issue 16, 2008, Pages 2518-2522

Novel synthetic approach to nine-membered diallylic amides: Stereochemical behavior and utility as chiral building block

Author keywords

Alkaloids; Amides; Asymmetric synthesis; Atropisomerism; Planar chirality

Indexed keywords

ALLYL COMPOUND; AMIDE;

EID: 54249093384     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078235     Document Type: Article
Times cited : (29)

References (35)
  • 1
    • 0002067180 scopus 로고
    • For reviews, see: a
    • For reviews, see: (a) Marshall, J. A. Acc. Chem. Res. 1980, 13, 213.
    • (1980) Acc. Chem. Res , vol.13 , pp. 213
    • Marshall, J.A.1
  • 5
    • 0034708730 scopus 로고    scopus 로고
    • For recent studies on planar chiral medium-sized rings, see: a
    • For recent studies on planar chiral medium-sized rings, see: (a) Sudau, A.; Munch, W.; Nubbemeyer, U. J. Org. Chem. 2000, 65, 1710.
    • (2000) J. Org. Chem , vol.65 , pp. 1710
    • Sudau, A.1    Munch, W.2    Nubbemeyer, U.3
  • 6
    • 0035026032 scopus 로고    scopus 로고
    • and references cited therein
    • (b) Nubbemeyer, U. Eur. J. Org. Chem. 2001, 1801; and references cited therein.
    • (2001) Eur. J. Org. Chem , pp. 1801
    • Nubbemeyer, U.1
  • 12
    • 78249281266 scopus 로고
    • For ring-closing-metathesis-based seven-membered lactam synthesis, see: a
    • For ring-closing-metathesis-based seven-membered lactam synthesis, see: (a) Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856.
    • (1993) J. Am. Chem. Soc , vol.115 , pp. 9856
    • Fu, G.C.1    Nguyen, S.T.2    Grubbs, R.H.3
  • 14
    • 54249152008 scopus 로고    scopus 로고
    • 1H NMR analysis of 6a and 6b revealed a trace amount of the aldehyde tautomer was contained (<5%).
    • 1H NMR analysis of 6a and 6b revealed a trace amount of the aldehyde tautomer was contained (<5%).
  • 15
    • 54249168693 scopus 로고    scopus 로고
    • 1H NMR).
    • 1H NMR).
  • 16
    • 54249124189 scopus 로고    scopus 로고
    • All new compounds were fully characterized by 1H NMR, 13C NMR, and IR spectroscopy. Data for Selected Compounds Compound 2b: 1H NMR (300 MHz, CDCl3, δ, 7.67 (d, J, 8.4 Hz, 2 H, 7.31 (d, J, 8.4 Hz, 2 H, 5.47 (ddd, J, 11.4, 10.8, 4.2 Hz, 1 H, 5.43-5.34 (m, 1 H, 5.24 (dd, J, 11.4, 4.5 Hz, 1 H, 4.26 (d, J, 9.9 Hz, 1 H, 3.89 (dd, J, 14.1, 4.2 Hz, 1 H, 3.05 (dd, J, 14.1, 10.8 Hz, 1 H, 3.00 (d, J, 9.9 Hz, 1 H, 2.44 (s, 3 H, 2.22-2.06 (m, 2 H, 1.99-1.70 (m, 2 H, 1.55 (s, 3 H, 13C NMR (75 MHz, CDCl3, δ, 143.0, 136.3, 134.2 (2 C, 132.2, 131.1, 129.7, 127.1, 59.0, 44.3, 27.0, 26.5, 21.7, 17.3. IR (reflection, 2934, 1597, 1452, 1324, 1158, 1095, 1023, 960, 869, 821, 767, 714, 658, 596 cm-1. Mp 123°C. For R-isomer(>98% ee, α]D27-65.3 c 0.80, CHCl3, for
    • 3)
  • 17
    • 54249089479 scopus 로고    scopus 로고
    • Analytical and semipreparative-scale HPLC were carried out with a chiral stationary column [CHIRALCEL OD-H (4.6 x 250 mm or 20 x 250 mm)] equipped with a UV detector and a CD spectropolarimeter.
    • Analytical and semipreparative-scale HPLC were carried out with a chiral stationary column [CHIRALCEL OD-H (4.6 x 250 mm or 20 x 250 mm)] equipped with a UV detector and a CD spectropolarimeter.
  • 18
    • 54249129447 scopus 로고    scopus 로고
    • The absolute configurations of 2b and 2c were speculated on the basis of the similarity of the CD spectra of 2a and 2d.
    • The absolute configurations of 2b and 2c were speculated on the basis of the similarity of the CD spectra of 2a and 2d.
  • 19
    • 54249165121 scopus 로고    scopus 로고
    • Enantioenriched 2 can be prepared via the fractional crystallization of its ammonium salt with chiral carboxylic acid, see ref. 3b.
    • Enantioenriched 2 can be prepared via the fractional crystallization of its ammonium salt with chiral carboxylic acid, see ref. 3b.
  • 20
    • 54249136445 scopus 로고    scopus 로고
    • The detailed transition-state analysis of racemization by ab initio calculation is in progress
    • The detailed transition-state analysis of racemization by ab initio calculation is in progress.
  • 21
    • 54249091274 scopus 로고    scopus 로고
    • The enantiopurity of 2a-d remains unchanged in the solid state(crystal) at -30°C for at least one year.
    • The enantiopurity of 2a-d remains unchanged in the solid state(crystal) at -30°C for at least one year.
  • 22
    • 0000241359 scopus 로고    scopus 로고
    • Pd(II)-catalyzed Cope rearrangement, see: Overman, L. E.; Jacobsen, E. J. J. Am. Chem. Soc. 1982, 104, 7225.
    • Pd(II)-catalyzed Cope rearrangement, see: Overman, L. E.; Jacobsen, E. J. J. Am. Chem. Soc. 1982, 104, 7225.
  • 23
    • 54249133127 scopus 로고    scopus 로고
    • The absolute stereochemistry of 10 was deduced from the configuration of 2b and the steric course of the reactions.
    • The absolute stereochemistry of 10 was deduced from the configuration of 2b and the steric course of the reactions.
  • 24
    • 0030911216 scopus 로고    scopus 로고
    • In general, the aza-Wittig rearrangement is considerably slower than the corresponding oxa-Wittig rearrangement. To enhance the reactivity of the aza-Wittig rearrangement, several contrivances have been developed. For reviews, see: a
    • In general, the aza-Wittig rearrangement is considerably slower than the corresponding oxa-Wittig rearrangement. To enhance the reactivity of the aza-Wittig rearrangement, several contrivances have been developed. For reviews, see: (a) Vogel, C. Synthesis 1997, 497.
    • (1997) Synthesis , pp. 497
    • Vogel, C.1
  • 25
    • 33645791244 scopus 로고    scopus 로고
    • Rappoport, Z, Marek, I, Eds, John Wiley and Sons: Chichester
    • (b) Tomooka, K. In The Chemistry of Organolithium Compounds, Vol. 2; Rappoport, Z.; Marek, I., Eds.; John Wiley and Sons: Chichester, 2004, 749-828.
    • (2004) The Chemistry of Organolithium Compounds , vol.2 , pp. 749-828
    • Tomooka, K.1
  • 26
    • 0000533321 scopus 로고    scopus 로고
    • The X-ray crystal structure analysis shows that the distance between C4 and C9 of 2a is 3.8 Å (Figure 2). The present rearrangement should proceed via a deprotonation of the C9 equatorial proton and an inversion of the configuration at the carbanion chiral center. It has been reported that [2,3]-Wittig rearrangement proceeds with inversion of configuration at the migrating terminus, see: (a) Verner, E. J.; Cohen, T. J. Am. Chem. Soc. 1992, 114, 375.
    • The X-ray crystal structure analysis shows that the distance between C4 and C9 of 2a is 3.8 Å (Figure 2). The present rearrangement should proceed via a deprotonation of the C9 equatorial proton and an inversion of the configuration at the carbanion chiral center. It has been reported that [2,3]-Wittig rearrangement proceeds with inversion of configuration at the migrating terminus, see: (a) Verner, E. J.; Cohen, T. J. Am. Chem. Soc. 1992, 114, 375.
  • 28
    • 0013608121 scopus 로고    scopus 로고
    • (+)-γ-Lycorane was obtained by Kotera in his degradation studies of lycorine, see: Kotera, K. Tetrahedron 1961, 12, 248.
    • (+)-γ-Lycorane was obtained by Kotera in his degradation studies of lycorine, see: Kotera, K. Tetrahedron 1961, 12, 248.
  • 29
    • 0028927235 scopus 로고    scopus 로고
    • Six different asymmetric syntheses of γ-lycorane(12) have been reported thus far, see: (a) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016.
    • Six different asymmetric syntheses of γ-lycorane(12) have been reported thus far, see: (a) Yoshizaki, H.; Satoh, H.; Sato, Y.; Nukui, S.; Shibasaki, M.; Mori, M. J. Org. Chem. 1995, 60, 2016.
  • 35
    • 54249139736 scopus 로고    scopus 로고
    • Mori and co-workers constructed the C ring of γ-lycorane by a Pd-catalyzed Mizoroki-Heck reaction, see ref. 18a.
    • Mori and co-workers constructed the C ring of γ-lycorane by a Pd-catalyzed Mizoroki-Heck reaction, see ref. 18a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.