메뉴 건너뛰기




Volumn 352, Issue 2-3, 2010, Pages 447-457

Copper-catalyzed asymmetric allylic alkylation of racemic cyclic substrates: Application of dynamic kinetic asymmetric transformation (DYKAT)

Author keywords

Allylic alkylation; Allylic compounds; Asymmetric catalysis; Copper; Nucleophilic substitution

Indexed keywords


EID: 77149149016     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.200900790     Document Type: Article
Times cited : (45)

References (95)
  • 7
    • 2442710925 scopus 로고    scopus 로고
    • N2′ see: a H. L. Goering, V. D. Singleton, J. Am. Chem. Soc. 1976, 98, 7854;
    • N2′ see: a) H. L. Goering, V. D. Singleton, J. Am. Chem. Soc. 1976, 98, 7854;
  • 37
    • 18744386668 scopus 로고    scopus 로고
    • Chem. Soc, For a review see
    • c) B. M. Trost, M. R. Machacek, H. C. Tsui, J. Am. Chem. Soc. 2005, 127, 7014. For a review see:
    • (2005) J. Am , vol.127 , pp. 7014
    • Trost, B.M.1    Machacek, M.R.2    Tsui, H.C.3
  • 39
    • 23944515252 scopus 로고    scopus 로고
    • For recent applications of DYKAT see: a
    • For recent applications of DYKAT see: a) E. Reyes, A. Cordova, Tetrahedron Lett. 2005, 46, 6605;
    • (2005) Tetrahedron Lett , vol.46 , pp. 6605
    • Reyes, E.1    Cordova, A.2
  • 46
    • 77149145615 scopus 로고    scopus 로고
    • 25: +77 [(c 1.0 in toluene, 100% ee) for (R)-3-ethylcyclohex-1-ene]. G. Buono, C. Siv, G. Peiffer, C. Triantaphylides, J. Org. Chem. 1985, 50, 1782;
    • 25: +77 [(c 1.0 in toluene, 100% ee) for (R)-3-ethylcyclohex-1-ene]. G. Buono, C. Siv, G. Peiffer, C. Triantaphylides, J. Org. Chem. 1985, 50, 1782;
  • 47
    • 11844260267 scopus 로고    scopus 로고
    • [9]), where the absolute configurations were wrongly assigned.
    • [9]), where the absolute configurations were wrongly assigned.
  • 55
    • 77149156070 scopus 로고    scopus 로고
    • Selected examples of process using a combination of biphosphine ligand and copper: a B. H. Lipshutz, H. Shimizu, Angew. Chem. 2004, 116, 2278;
    • Selected examples of process using a combination of biphosphine ligand and copper: a) B. H. Lipshutz, H. Shimizu, Angew. Chem. 2004, 116, 2278;
  • 67
    • 77149170469 scopus 로고    scopus 로고
    • The authors thank Prof. Dr. J. P. Genêt and Dr. V. Vidal-Ratovelomanana for a generous gift of ligands L12 and L13
    • The authors thank Prof. Dr. J. P. Genêt and Dr. V. Vidal-Ratovelomanana for a generous gift of ligands L12 and L13.
  • 68
    • 77149158236 scopus 로고    scopus 로고
    • Ligands L14 to L17 were generously donated by Solvias.
    • Ligands L14 to L17 were generously donated by Solvias.
  • 69
    • 77149175759 scopus 로고    scopus 로고
    • See Experimental Section
    • See Experimental Section.
  • 70
    • 0035805286 scopus 로고    scopus 로고
    • According to the work of Bäckvall, the reaction of allylmagnesium bromide led to poor conversion and low ee (60% after 18 h, 54% ee). A. S. E. Karlstrom, J. E. Bäckvall, Chem. Eur. J. 2001, 7, 1981.
    • According to the work of Bäckvall, the reaction of allylmagnesium bromide led to poor conversion and low ee (60% after 18 h, 54% ee). A. S. E. Karlstrom, J. E. Bäckvall, Chem. Eur. J. 2001, 7, 1981.
  • 71
    • 77149159854 scopus 로고    scopus 로고
    • 31P NMR, showed that the chiral ligand was damaged.
    • 31P NMR, showed that the chiral ligand was damaged.
  • 72
    • 77149127498 scopus 로고    scopus 로고
    • To determine the absolute configuration of the products stemming from the addition of secondary or tertiary alkyl-Grignard reagents to substrate 6, the following procedure was carried out. 3-(S)-Cyclohexyl-1,7- octadiene (78% ee) was prepared according to a reported procedure, K. Tissot-Croset, D. Polet, S. Gille, C. Hawner, A. Alexakis, Angew. Chem. 2004, 116, 2480-2482;
    • To determine the absolute configuration of the products stemming from the addition of secondary or tertiary alkyl-Grignard reagents to substrate 6, the following procedure was carried out. 3-(S)-Cyclohexyl-1,7- octadiene (78% ee) was prepared according to a reported procedure. (K. Tissot-Croset, D. Polet, S. Gille, C. Hawner, A. Alexakis, Angew. Chem. 2004, 116, 2480-2482;
  • 73
    • 3042695125 scopus 로고    scopus 로고
    • [9]), where the absolute configurations were wrongly assigned.
    • [9]), where the absolute configurations were wrongly assigned.
  • 74
    • 0027240732 scopus 로고    scopus 로고
    • [1b]
    • [1b]
  • 75
    • 77149142358 scopus 로고    scopus 로고
    • Selected examples of Cu-catalyzed asymmetric allylic methylation: a U. Piarulli, P. Daubos, C. Claverie, M. Roux, C. Gennari, Angew. Chem. 2003, 115, 244;
    • Selected examples of Cu-catalyzed asymmetric allylic methylation: a) U. Piarulli, P. Daubos, C. Claverie, M. Roux, C. Gennari, Angew. Chem. 2003, 115, 244;
  • 82
    • 0035802951 scopus 로고    scopus 로고
    • For information about DKR and DYKAT see: a
    • For information about DKR and DYKAT see: a) K. Faber, Chem. Eur. J. 2001, 7, 5004;
    • (2001) Chem. Eur. J , vol.7 , pp. 5004
    • Faber, K.1
  • 86
    • 34250781380 scopus 로고    scopus 로고
    • For an example of the use of styrene as radical scavenger see
    • For an example of the use of styrene as radical scavenger see: K. Y. Li, A. Alexakis, Angew. Chem. 2006, 118, 7762;
    • (2006) Angew. Chem , vol.118 , pp. 7762
    • Li, K.Y.1    Alexakis, A.2
  • 89
    • 77149168263 scopus 로고    scopus 로고
    • In particular cases the leaving group avoids the formation of a p-allyl, see ref.[2g
    • [2g]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.