메뉴 건너뛰기




Volumn 48, Issue 27, 2009, Pages 5026-5029

Direct catalytic asymmetric mannich-type reaction of thioamides

Author keywords

Asymmetric catalysis; Copper; Mannich reactions; Proton transfer; Thioamides

Indexed keywords

ASYMMETRIC CATALYSIS; COOPERATIVE CATALYSIS; LEWIS ACID; MANNICH REACTIONS; MANNICH-TYPE REACTIONS; PRONUCLEOPHILES; THIOAMIDES;

EID: 70349931503     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200901588     Document Type: Article
Times cited : (62)

References (44)
  • 1
    • 0037239881 scopus 로고    scopus 로고
    • and references therein
    • T.S. Jagodzinski, Chem. Rev. 2003, 103, 197, and references therein.
    • (2003) Chem. Rev. , vol.103 , pp. 197
    • Jagodzinski, T.S.1
  • 9
    • 0026418434 scopus 로고
    • a) B. M. Trost, Science 1991, 254, 1471;
    • (1991) Science , vol.254 , pp. 1471
    • Trost, B.M.1
  • 11
    • 20344364640 scopus 로고    scopus 로고
    • For the utility of N-diphenylphosphinoyl imines, see: a) S. M. Weinreb, R. K. Orr, Synthesis 2005. 1205:
    • (2005) Synthesis , pp. 1205
    • Weinreb, S.M.1    Orr, R.K.2
  • 13
    • 33746204727 scopus 로고    scopus 로고
    • For recent reviews on direct Mannich(-type) reactions, see: a) M. M. B. Marques. Angew. Chem. 2006, 118, 356;
    • (2006) Angew. Chem. , vol.118 , pp. 356
    • Marques, M.M.B.1
  • 17
    • 10844266525 scopus 로고    scopus 로고
    • (Eds.: E.N. Jacobsen, A. Pfaltz, H. Yamamoto). Springer, Berlin. Chapter 29.5
    • for general reviews on catalytic asymmetric Mannich reactions, see: d) S. Kobayashi, M. Ueno in Comprehensive Asymmetric Catalysis, Supplement 1 (Eds.: E.N. Jacobsen, A. Pfaltz, H. Yamamoto). Springer, Berlin. 2004, Chapter 29.5, p. 143;
    • (2004) Comprehensive Asymmetric Catalysis , Issue.SUPPL. 1 , pp. 143
    • Kobayashi, S.1    Ueno, M.2
  • 29
    • 0003438540 scopus 로고
    • Cornel University, Ithaca, NY
    • Sulfur has an electronegativity close to that for carbon: a) L. Pauling in The Nature of Chemical Bond, 3rd ed., Cornel University, Ithaca, NY, 1960, pp. 88;
    • (1960) The Nature of Chemical Bond, 3rd Ed. , pp. 88
    • Pauling, L.1
  • 30
    • 0039569428 scopus 로고
    • for rotational barriers of thioamides, see: b) C. M. Lee, W. D. Kumler, J. Org. Chem. 1962, 27, 2052;
    • (1962) J. Org. Chem. , vol.27 , pp. 2052
    • Lee, C.M.1    Kumler, W.D.2
  • 39
    • 70349951089 scopus 로고    scopus 로고
    • note
    • As of May 2009, this commercially available C2 unit sells for ε85.7 per 5 g from A Better Choice for Research Chemicals.
  • 41
    • 70349960458 scopus 로고    scopus 로고
    • The absolute configuration of 3 ab was determined by single Xray crystallographic analysis. Mr = 475.67, colorless block; a = 13.9241(3), b = 19.8931(4). c = 21.3053(4) Å, α = 64.6031(10)°, β= 118.497(7)°, γ = 88.5534(11)°. V=5228.95(19) Å, T= 103 K, triclinic, space group P1, Z = 8, Rigaku RAXIS-RAPID, λ(Cu Kα) = 1.54187 Å, 0max = 68.25°. The crystallographic data (CCDC-720992) can be obtained free of charge from The Cambridge Crystallogrpahic Data Center via www.ccdc.cam. ac.uk/data-request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.