메뉴 건너뛰기




Volumn 47, Issue 39, 2008, Pages 7515-7519

Divergent titanium-mediated allylations with modulation by nickel or palladium

Author keywords

Allylation; Carbocycles; Nickel; Palladium; Titanium

Indexed keywords


EID: 54749131070     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200802520     Document Type: Article
Times cited : (59)

References (45)
  • 1
    • 0040155755 scopus 로고    scopus 로고
    • For a seminal work on titanocene(III) chemistry see: T. V. Rajan Babu, W. A. Nugent, J. Am. Chem. Soc. 1994, 116, 986-997.
    • For a seminal work on titanocene(III) chemistry see: T. V. Rajan Babu, W. A. Nugent, J. Am. Chem. Soc. 1994, 116, 986-997.
  • 4
    • 0032539234 scopus 로고    scopus 로고
    • Selected references: a A. Gansäuer, H. Bluhm, M. Pierobon, J. Am. Chem. Soc. 1998, 120, 12849-12859;
    • Selected references: a) A. Gansäuer, H. Bluhm, M. Pierobon, J. Am. Chem. Soc. 1998, 120, 12849-12859;
  • 8
    • 33748636029 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 5522-5526.
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 5522-5526
  • 12
    • 0000048482 scopus 로고
    • Eds, B. M. Trost, I. Fleming, Pergamon, Oxfod, chap. 1.2;
    • a) W. Oppolzer in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxfod, 1991, chap. 1.2;
    • (1991) Comprehensive Organic Synthesis , vol.5
    • Oppolzer, W.1
  • 16
    • 0001344148 scopus 로고    scopus 로고
    • W . Oppolzer, M. Bedoya-Zurita, C. Y. Switzer, Tetrahedron Lett. 1988, 29, 6433-6436.
    • W . Oppolzer, M. Bedoya-Zurita, C. Y. Switzer, Tetrahedron Lett. 1988, 29, 6433-6436.
  • 17
    • 54749138104 scopus 로고    scopus 로고
    • For experimental details see Supporting Information
    • For experimental details see Supporting Information.
  • 18
    • 54749144680 scopus 로고    scopus 로고
    • Addition of triphenylphosphine considerably increased the yields, possibly stabilizing palladium intermediates
    • Addition of triphenylphosphine considerably increased the yields, possibly stabilizing palladium intermediates.
  • 19
    • 54749129049 scopus 로고    scopus 로고
    • The anti configuration of 2 was tentatively assigned on the basis of the stereochemical behavior evident in the closely related allylation of decanal with (E)-but-2-enyl ethyl carbonate promoted by Pd/Ti (Table 1, entry 11).
    • The anti configuration of 2 was tentatively assigned on the basis of the stereochemical behavior evident in the closely related allylation of decanal with (E)-but-2-enyl ethyl carbonate promoted by Pd/Ti (Table 1, entry 11).
  • 20
    • 0000337182 scopus 로고    scopus 로고
    • W . Oppolzer, T. H. Keller, M. Bedoya-Zurita, C. Stone, Tetrahedron Lett. 1989, 30, 5883-5886.
    • W . Oppolzer, T. H. Keller, M. Bedoya-Zurita, C. Stone, Tetrahedron Lett. 1989, 30, 5883-5886.
  • 22
    • 0000012889 scopus 로고    scopus 로고
    • Selected references: a T. Tabuchi, J. Inanaga, M. Yamaguchi, Tetrahedron Lett. 1986, 27, 1195-1196;
    • Selected references: a) T. Tabuchi, J. Inanaga, M. Yamaguchi, Tetrahedron Lett. 1986, 27, 1195-1196;
  • 30
    • 54749096019 scopus 로고    scopus 로고
    • III-promoted Wurtz-type reaction of farnesyl ethyl carbonate, obtaining squalene (81%) with acceptable regio- and stereoselectivity. For details, see Supporting Information.
    • III-promoted Wurtz-type reaction of farnesyl ethyl carbonate, obtaining squalene (81%) with acceptable regio- and stereoselectivity. For details, see Supporting Information.
  • 31
    • 0000334212 scopus 로고
    • For selected references of closely related nucleophilic allyltitanium complexes: a
    • For selected references of closely related nucleophilic allyltitanium complexes: a) A. Kasatkin, T. Nakagawa, S. Okamoto, F. Sato, J. Am. Chem. Soc. 1995, 117, 3881-3882;
    • (1995) J. Am. Chem. Soc , vol.117 , pp. 3881-3882
    • Kasatkin, A.1    Nakagawa, T.2    Okamoto, S.3    Sato, F.4
  • 33
    • 37049089453 scopus 로고    scopus 로고
    • In any case, alternative mechanisms based on nucleophilic allylpalladium complexes cannot be completely ruled out; see: a H. Nakamura, N. Asao, Y. Yamamoto, J. Chem. Soc. Chem. Commun. 1995, 1273-1274;
    • In any case, alternative mechanisms based on nucleophilic allylpalladium complexes cannot be completely ruled out; see: a) H. Nakamura, N. Asao, Y. Yamamoto, J. Chem. Soc. Chem. Commun. 1995, 1273-1274;
  • 37
    • 2442609566 scopus 로고    scopus 로고
    • Exoc yclic alkene 4 is reminiscent of products obtained in the Oppolzer cyclization. It should be noted, however, that nickel catalysts have seldom been used for this transformation, possibly because it is not easy to reintroduce them into a catalytic cycle; see: B.-L. Lin, L. Liu, Y. Fu, S.-W. Luo, Q. Chen, Q.-X. Guo, Organometallics 2004, 23, 2114-2123.
    • Exoc yclic alkene 4 is reminiscent of products obtained in the Oppolzer cyclization. It should be noted, however, that nickel catalysts have seldom been used for this transformation, possibly because it is not easy to reintroduce them into a catalytic cycle; see: B.-L. Lin, L. Liu, Y. Fu, S.-W. Luo, Q. Chen, Q.-X. Guo, Organometallics 2004, 23, 2114-2123.
  • 38
    • 0000159852 scopus 로고    scopus 로고
    • This excellent stereoselectivity is considerably higher than that reported for related cyclizations based on titanium(II) and zirconium(II, complexes; see: a) T. Takahashi, D. Y. Kondakov, N. Suzuki, Organometallics 1994, 13, 3411-3412;
    • This excellent stereoselectivity is considerably higher than that reported for related cyclizations based on titanium(II) and zirconium(II)- complexes; see: a) T. Takahashi, D. Y. Kondakov, N. Suzuki, Organometallics 1994, 13, 3411-3412;
  • 43
    • 0028135651 scopus 로고    scopus 로고
    • Previous ly reported procedures to prepare similar carbocycles afforded lower yields and poorer chemical compatibility; see: a W. Oppolzer, F. Schröder, Tetrahedron Lett. 1994, 35, 7939-7942;
    • Previous ly reported procedures to prepare similar carbocycles afforded lower yields and poorer chemical compatibility; see: a) W. Oppolzer, F. Schröder, Tetrahedron Lett. 1994, 35, 7939-7942;
  • 45
    • 33845279655 scopus 로고    scopus 로고
    • 3SnH-induced radical cyclization of an allylic bromide closely related to carbonate 1 provided considerably worse regio- (91:9 5-exo/6-endo) and stereoselectivity (cis/trans, 65:35) than those afforded by the Ni/Ti system; see: G. Stork, M. E. Reynolds, J. Am. Chem. Soc. 1988, 110, 6911-6913.
    • 3SnH-induced radical cyclization of an allylic bromide closely related to carbonate 1 provided considerably worse regio- (91:9 5-exo/6-endo) and stereoselectivity (cis/trans, 65:35) than those afforded by the Ni/Ti system; see: G. Stork, M. E. Reynolds, J. Am. Chem. Soc. 1988, 110, 6911-6913.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.