Palladium catalyzed allylation is under stereoelectronic control

Arkivoc

Volumn 2001, Issue 1, 2001, Pages 269-276

  Bates, Roderick W ^a   Kongsaeree, Palangpon ^b   Nontapattamadul, Nunth ^a,c  

^a CHULABHORN RESEARCH INSTITUTE   (Thailand)

^b MAHIDOL UNIVERSITY   (Thailand)

^c CHULALONGKORN UNIVERSITY   (Thailand)

Author keywords

Allylation; Palladium; Stereoelectronic

Indexed keywords

KETONE DERIVATIVE; MENTHONE; PALLADIUM;

ALLYLATION; ANALYTIC METHOD; ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHIRALITY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 3042781293     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

1. Trost, B.M.; van Vranken, D.L. Chem.Rev. 1996, 96, 395; J.M.J.Williams, Catalysis in Organic Synthesis, Sheffield Academic Press, Sheffield, 1999, p.154.
2. Trost, B.M.; van Vranken, D.L. Chem.Rev. 1996, 96, 395; J.M.J.Williams, Catalysis in Organic Synthesis, Sheffield Academic Press, Sheffield, 1999, p.154.
3. Heumann, A.; Réglier, M. Tetrahedron 1995, 51, 975; Hayashi, T.; Yamamoto, A.; Hagihara, T. J.Org.Chem. 1986, 51, 723; Farthing, C.N.; Kocovsky, P. J.Am.Chem.Soc. 1998, 120, 6661; Trost, B.M.; Verhoeven, T.R. J.Org.Chem. 1976, 41, 3215; J.Am.Chem.Soc. 1980, 102, 4730.
4. Heumann, A.; Réglier, M. Tetrahedron 1995, 51, 975; Hayashi, T.; Yamamoto, A.; Hagihara, T. J.Org.Chem. 1986, 51, 723; Farthing, C.N.; Kocovsky, P. J.Am.Chem.Soc. 1998, 120, 6661; Trost, B.M.; Verhoeven, T.R. J.Org.Chem. 1976, 41, 3215; J.Am.Chem.Soc. 1980, 102, 4730.
5. Heumann, A.; Réglier, M. Tetrahedron 1995, 51, 975; Hayashi, T.; Yamamoto, A.; Hagihara, T. J.Org.Chem. 1986, 51, 723; Farthing, C.N.; Kocovsky, P. J.Am.Chem.Soc. 1998, 120, 6661; Trost, B.M.; Verhoeven, T.R. J.Org.Chem. 1976, 41, 3215; J.Am.Chem.Soc. 1980, 102, 4730.
6. Heumann, A.; Réglier, M. Tetrahedron 1995, 51, 975; Hayashi, T.; Yamamoto, A.; Hagihara, T. J.Org.Chem. 1986, 51, 723; Farthing, C.N.; Kocovsky, P. J.Am.Chem.Soc. 1998, 120, 6661; Trost, B.M.; Verhoeven, T.R. J.Org.Chem. 1976, 41, 3215; J.Am.Chem.Soc. 1980, 102, 4730.
7. Heumann, A.; Réglier, M. Tetrahedron 1995, 51, 975; Hayashi, T.; Yamamoto, A.; Hagihara, T. J.Org.Chem. 1986, 51, 723; Farthing, C.N.; Kocovsky, P. J.Am.Chem.Soc. 1998, 120, 6661; Trost, B.M.; Verhoeven, T.R. J.Org.Chem. 1976, 41, 3215; J.Am.Chem.Soc. 1980, 102, 4730.
8. It has been shown that arylation using lead reagents gives the axial product: Elliott, G.I., Konopelski, J.P., Olmstead, M.M., Organic Letters, 1999, 1, 1867.
9. Preparation from menthone: Tanaka, A.; Tanaka, R.; Uda, H.; Yoshikoshi, A. J.Chem.Soc. Perkin I 1972, 1721. Determination of stereochemistry: LeCloux, D.D.; Tolman, W.B. J.Am.Chem.Soc. 1993, 115, 1153.
10. Preparation from menthone: Tanaka, A.; Tanaka, R.; Uda, H.; Yoshikoshi, A. J.Chem.Soc. Perkin I 1972, 1721. Determination of stereochemistry: LeCloux, D.D.; Tolman, W.B. J.Am.Chem.Soc. 1993, 115, 1153.
11. Trost, B.M.; Runge, T.A. J.Am.Chem.Soc. 1981, 103, 7550; Trost, B.M.; Runge, T.A.; Jungheim, L.N. J.Am.Chem.Soc. 1980, 102, 2840. Allylation of 1 using allyl bromide and base without Pd yields mixtures of O- and C-allylated products.
12. Trost, B.M.; Runge, T.A. J.Am.Chem.Soc. 1981, 103, 7550; Trost, B.M.; Runge, T.A.; Jungheim, L.N. J.Am.Chem.Soc. 1980, 102, 2840. Allylation of 1 using allyl bromide and base without Pd yields mixtures of O- and C-allylated products.
13. Details have been deposited with the Cambridge Crystallographic Database: number CCDC 162773.
14. Deslongchamps, P., Stereoelectronic Effects in Organic Chemistry, Pergamon Press, Oxford, 1983, pp 280-284.
15. Dauben, W.G.; Hart, D.J. J.Am.Chem.Soc. 1977, 99, 7307; Petrow, V.A. J.Chem.Soc. 1942, 693. Compound 6 was entirely enolized.
16. Dauben, W.G.; Hart, D.J. J.Am.Chem.Soc. 1977, 99, 7307; Petrow, V.A. J.Chem.Soc. 1942, 693. Compound 6 was entirely enolized.
17. 3).
18. 3).
19. Özbal, H.; Zajac, Jr., W.W. Tetrahedron Lett. 1979, 4821. Compound 8 was obtained as a mixture of diastereoisomers.
20. Boone, J.R.; Ashby, E.C. Top. Stereochem. 1979, 11, 53.
21. Bates, R.W.; Kongsaeree, P; Nontapattamadul N., Theerasilp, M., in preparation.
22. Heck, R.F., Palladium Reagents in Organic Synthesis, Academic Press, 1985, p 3.