메뉴 건너뛰기




Volumn 43, Issue 44, 2004, Pages 5971-5973

Readily available biaryl P,N ligands for asymmetric catalysis

Author keywords

Asymmetric catalysis; Atropisomerism; Heterocycles; Hydroboration; P,N ligands

Indexed keywords

AMINES; CATALYSIS; OXYGEN; PALLADIUM;

EID: 9344245165     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461286     Document Type: Article
Times cited : (340)

References (32)
  • 1
    • 0003445429 scopus 로고    scopus 로고
    • (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin
    • Comprehensive Asymmetric Catalysis, Vol. 1-3 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999.
    • (1999) Comprehensive Asymmetric Catalysis, Vol. 1-3 , vol.1-3
  • 4
    • 0242269462 scopus 로고    scopus 로고
    • c) For an extensive review on P,N Ligands with pyridine donors, see: G. Chelucci, G. Orru, G. A. Pinna, Tetrahedron 2003, 59, 9471-9515.
    • (2003) Tetrahedron , vol.59 , pp. 9471-9515
    • Chelucci, G.1    Orru, G.2    Pinna, G.A.3
  • 5
    • 9344250383 scopus 로고    scopus 로고
    • note
    • Quinap: 1-(2-diphenylphosphino-1-naphthyl)isoquinoline.
  • 9
    • 0346243940 scopus 로고    scopus 로고
    • c) N. Gommermann, C. Koradin, K. Polborn, P. Knochel, Angew. Chem. 2003, 115, 5941-5944; Angew. Chem. Int. Ed. 2003, 42, 5763-5766;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 5763-5766
  • 12
    • 9344222627 scopus 로고    scopus 로고
    • note
    • We suggest the acronym pinap in analogy to quinap, where "pi" refers to phthalazine.
  • 15
    • 9344266174 scopus 로고    scopus 로고
    • note
    • 50 mg (P)- or (M)-quinap costs € 143 at STREM.
  • 17
    • 9344234254 scopus 로고    scopus 로고
    • note
    • Depending on the scale, different separation procedures were applied. Typically on > 2 g scale either 3a or 5a was selectively crystallized from the mixture (see Supporting Information for details), and the residue was purified by flash chromatography. On a smaller scale the diastereomers were separated by flash chromatography; for example, 1.21 g of a mixture of 3a/3b was separated by flash chromatography to give 3a (595 mg) and 3b (501 mg; 91% mass recovery).
  • 18
    • 9344258434 scopus 로고    scopus 로고
    • note
    • CCDC-243850 (3a) and CCDC-243851 (5a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
  • 22
    • 33748511263 scopus 로고
    • c) A. Schnyder, L. Hintermann, A. Togni, Angew. Chem. 1995, 107, 628-630; Angew. Chem. Int. Ed. Engl. 1995, 34, 931-933.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 931-933
  • 23
    • 9344227173 scopus 로고    scopus 로고
    • note
    • Ligand 3b gave slightly lower enantioselectivities (89% ee in the hydroboration of styrene). The complexes with ligands 5a and 5b gave lower enantioselectivities and yields.
  • 25
    • 9344265011 scopus 로고    scopus 로고
    • note
    • Ligand 3b gave slightly lower enantioselectivities (93% ee for R = CN). The complexes with ligands 5a and 5b gave lower enantioselectivities and yields.
  • 32
    • 9344262758 scopus 로고    scopus 로고
    • note
    • Ligands 3a and 3b gave comparable results (for R = iPr and R′ = Ph; 3a: 92% ee (R) and 3b: 94% ee (S)).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.