메뉴 건너뛰기




Volumn 47, Issue 2, 2008, Pages 398-401

Catalytic enantioselective 1,6-conjugate addition of Grignard reagents to linear dienoates

Author keywords

1,6 Conjugate addition; Asymmetric catalysis; Copper; Enantioselectivity; Grignard reaction

Indexed keywords

CATALYSTS; COPPER; ENANTIOSELECTIVITY; SUBSTITUTION REACTIONS;

EID: 38049058696     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200703702     Document Type: Article
Times cited : (110)

References (49)
  • 4
    • 0000679263 scopus 로고    scopus 로고
    • Recent reviews: a, Eds, E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, New York
    • Recent reviews: a) K. Tomioka, Y. Nagaoka, Comprehensive Asymmetric Catalysis, Vol. 3 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York, 1999, pp. 1105-1120;
    • (1999) Comprehensive Asymmetric Catalysis , vol.3 , pp. 1105-1120
    • Tomioka, K.1    Nagaoka, Y.2
  • 13
    • 24844465309 scopus 로고    scopus 로고
    • First example of 1,6-selectivity: F. Näf, P. Degen, G. Ohloff, Helv. Chim. Acta 1972, 55, 82-85.
    • First example of 1,6-selectivity: F. Näf, P. Degen, G. Ohloff, Helv. Chim. Acta 1972, 55, 82-85.
  • 14
    • 0005908712 scopus 로고
    • For enynes
    • For enynes: N. Krause, Chem. Ber. 1990, 123, 2173-2180.
    • (1990) Chem. Ber , vol.123 , pp. 2173-2180
    • Krause, N.1
  • 15
    • 11144342196 scopus 로고    scopus 로고
    • Recently, other metals have been used to obtain 1,6-addition products. For Fe: a K. Fukuhara, H. Urabe, Tetrahedron Lett. 2005, 46, 603-606;
    • Recently, other metals have been used to obtain 1,6-addition products. For Fe: a) K. Fukuhara, H. Urabe, Tetrahedron Lett. 2005, 46, 603-606;
  • 16
    • 29444458959 scopus 로고    scopus 로고
    • for Rh: b G. de la Hérran, C. Murcia, A. G. Csákÿ, Org. Lett. 2005, 7, 5629-5632;
    • for Rh: b) G. de la Hérran, C. Murcia, A. G. Csákÿ, Org. Lett. 2005, 7, 5629-5632;
  • 17
    • 38049075506 scopus 로고    scopus 로고
    • for Ir: c T. Nishimura, Y. Yasuhara, T. Hayashi, Angew. Chem. 2006, 118, 5288-5290;
    • for Ir: c) T. Nishimura, Y. Yasuhara, T. Hayashi, Angew. Chem. 2006, 118, 5288-5290;
  • 18
    • 33747229725 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 5164-5166.
    • (2006) Chem. Int. Ed , vol.45 , pp. 5164-5166
    • Angew1
  • 19
    • 0842285210 scopus 로고    scopus 로고
    • Stereoselective addition has been achieved for enynes: T. Hayashi, N. Tokunaga, K. Inoue, Org. Lett. 2004, 6, 305-307.
    • Stereoselective addition has been achieved for enynes: T. Hayashi, N. Tokunaga, K. Inoue, Org. Lett. 2004, 6, 305-307.
  • 21
    • 22144458723 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4224-4227.
    • (2005) Chem. Int. Ed , vol.44 , pp. 4224-4227
    • Angew1
  • 22
    • 38049013143 scopus 로고    scopus 로고
    • For β-unsubstituted dienones regioselectivity drops to 70
    • For β-unsubstituted dienones regioselectivity drops to 70%.
  • 25
    • 38049086466 scopus 로고    scopus 로고
    • The Cu-catalyzed 1,6-ACA to 2,4-dienones has been studied and gave a mixture of 1,2- and 1,6-addition products. Studies to optimize these results are underway.
    • The Cu-catalyzed 1,6-ACA to 2,4-dienones has been studied and gave a mixture of 1,2- and 1,6-addition products. Studies to optimize these results are underway.
  • 28
    • 23044467079 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4715-4719;
    • (2005) Chem. Int. Ed , vol.44 , pp. 4715-4719
    • Angew1
  • 33
    • 18844403662 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 2752-2756;
    • (2005) Chem. Int. Ed , vol.44 , pp. 2752-2756
    • Angew1
  • 35
    • 38049038649 scopus 로고    scopus 로고
    • No other esters have been studied for comparison purposes
    • No other esters have been studied for comparison purposes.
  • 36
    • 38049041764 scopus 로고    scopus 로고
    • Mainly degradation of starting material was observed
    • Mainly degradation of starting material was observed.
  • 39
    • 38049069023 scopus 로고    scopus 로고
    • Formation of the 1,4-addition product with high enantioselectivity at -70°C hints that σ complex 11 is an intermediate in the 1,6-addition mechanism. Further investigation is needed to confirm this hypothesis.
    • Formation of the 1,4-addition product with high enantioselectivity at -70°C hints that σ complex 11 is an intermediate in the 1,6-addition mechanism. Further investigation is needed to confirm this hypothesis.
  • 40
    • 38049061901 scopus 로고    scopus 로고
    • [15] Further research is needed to identify the rate-determining step for this catalytic cycle.
    • [15] Further research is needed to identify the rate-determining step for this catalytic cycle.
  • 41
    • 38049095939 scopus 로고    scopus 로고
    • Freshly prepared Grignard reagents should be used to obtain good yields
    • Freshly prepared Grignard reagents should be used to obtain good yields.
  • 42
    • 38049050928 scopus 로고    scopus 로고
    • In entry 3 of Table 4 19c is present in varying amounts (35-50%).
    • In entry 3 of Table 4 19c is present in varying amounts (35-50%).
  • 44
    • 33845219123 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7506-7525;
    • (2006) Chem. Int. Ed , vol.45 , pp. 7506-7525
    • Angew1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.