Catalytic asymmetrization of racemic dicyclopentadiene derivatives by using chiral copper(II) catalyst

Enantiomer

Volumn 5, Issue 1, 2000, Pages 47-61

  Kohmura, Y ^a   Katsuki, T ^a  

^a NONE

Author keywords

Allylic oxidation; Chiral copper(II) complex; Dicyclopentadiene derivatives; Kharash Sosnovsky reaction; Oxidative asymmetrization; Tris(oxazoline) ligand

Indexed keywords

ACETONITRILE; ALKADIENE; COPPER ION; DICYCLOPENTADIENE DERIVATIVE; OXAZOLINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHIRALITY; CONTROLLED STUDY; DRUG ANALYSIS; DRUG CONFORMATION; DRUG OXIDATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034103917     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (21)

1. For the review on the use of chiral dicyclopentadienes in organic synthesis, see: (a) K. Ogasawara, Pure and Appl. Chem. 1994, 66, 2119-2122; (b) K. Ogasawara, J. Syn. Org. Chem. Jpn. 1996, 54, 29-40.
2. For the review on the use of chiral dicyclopentadienes in organic synthesis, see: (a) K. Ogasawara, Pure and Appl. Chem. 1994, 66, 2119-2122; (b) K. Ogasawara, J. Syn. Org. Chem. Jpn. 1996, 54, 29-40.
3. For the review of transition metal-catalyzed asymmetric allylic substitution, see: (a) T. Hayashi, In I. Ojima, Ed., Catalytic Asymmetric Synthesis. VCH publishers, Inc., New York, (1993), pp 325-365; (b) B.M. Trost and D.L. Van Vranken, Chem. Rev. 1996, 96, 395-422; M. Johannsen and K.A. Jørgensen, Chem. Rev. 1998, 98, 1689-1708.
4. For the review of transition metal-catalyzed asymmetric allylic substitution, see: (a) T. Hayashi, In I. Ojima, Ed., Catalytic Asymmetric Synthesis. VCH publishers, Inc., New York, (1993), pp 325-365; (b) B.M. Trost and D.L. Van Vranken, Chem. Rev. 1996, 96, 395-422; M. Johannsen and K.A. Jørgensen, Chem. Rev. 1998, 98, 1689-1708.
5. For the review of transition metal-catalyzed asymmetric allylic substitution, see: (a) T. Hayashi, In I. Ojima, Ed., Catalytic Asymmetric Synthesis. VCH publishers, Inc., New York, (1993), pp 325-365; (b) B.M. Trost and D.L. Van Vranken, Chem. Rev. 1996, 96, 395-422; M. Johannsen and K.A. Jørgensen, Chem. Rev. 1998, 98, 1689-1708.
6. (a) M.S. Kharasch and G. Sosnovsky, J. Am. Chem. Soc. 1958, 80, 756;
7. (b) M.S. Kharasch and A. Fono, J. Org. Chem. 1958, 23, 324;
8. (c) For the review of oxidation using a combination of copper complex and peroxyester, see: D.J. Rawlinson and G. Sosnovsky, Synthesis 1972, 1-28.
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14. (b) K. Kawasaki and T. Katsuki, Tetrahedron 1997, 53, 6337-6350.
15. A preliminary result of this study has been communicated: Y. Kohmura and T. Katsuki, Synlett. (in press).
16. T. Ogino and K. Mochizuki, Chem. Lett. 1979, 443-446.
17. S. Takano, M. Moriya, K. Tanaka and K. Ogasawara, Synthesis 1994, 687-688.
18. 1= 0.076, Rw=0.056 for 1027 reflections and 218 variables, GOF=2.89. Data were collected on a Rigaku RAXIS RAPID imaging plate area detector with graphite monochromated Mo-Kα (λ=0.71069 Å) at -90°C. Structural analysis was performed using the teXsan crystallographic software package.
19. Although the bond dissociation energy of methine C-H bond is known to be smaller than methylene C-H bond, we expected that the abstraction of methylene hydrogen atom by bulky butoxy radical would occur in preference to methine hydrogen atom, since the bridgehead methine carbon is more sterically crowded and the abstraction of the methine hydrogen atom generates more strained allyl radical intermediate than the intermediate obtained by abstraction of the methylene hydrogen atom.
20. Olefins are known to coordinate to cationic copper ion: (a) R. Quan, Z. Li and E.N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 8156-8157; (b) M.M.-C. Lo and G.C. Fu, J. Am. Chem. Soc. 1998, 120, 10270-10271.
21. Olefins are known to coordinate to cationic copper ion: (a) R. Quan, Z. Li and E.N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 8156-8157; (b) M.M.-C. Lo and G.C. Fu, J. Am. Chem. Soc. 1998, 120, 10270-10271.