메뉴 건너뛰기




Volumn 45, Issue 9, 2006, Pages 1432-1435

Remote chiral induction in the organocatalytic hydrosilylation of aromatic ketones and ketimines

Author keywords

Arene arene interactions; Asymmetric catalysis; N ligands; Organocatalysis; Reduction

Indexed keywords

ARENE-ARENE INTERACTIONS; ASYMMETRIC CATALYSIS; N LIGANDS; ORGANOCATALYSIS;

EID: 33745661731     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503941     Document Type: Article
Times cited : (142)

References (45)
  • 26
    • 3142759422 scopus 로고    scopus 로고
    • A very efficient organocatalytic protocol for the hydrosilylation of ketimines (with ≤92% ee) has been developed by us recently: a) A. V. Malkov, A. Mariani, K. MacDougall, P. Kočovský, Org. Lett. 2004, 6, 2253;
    • (2004) Org. Lett. , vol.6 , pp. 2253
    • Malkov, A.V.1    Mariani, A.2    MacDougall, K.3    Kočovský, P.4
  • 34
    • 84984369511 scopus 로고
    • Hydrosilylation of 1a, catalyzed by Rh complexes of 5 and 6, produced alcohol 2a in 69% ee and 9% ee, respectively: H. Brunner, U. Obermann, Chem. Ber. 1989, 122, 499.
    • (1989) Chem. Ber. , vol.122 , pp. 499
    • Brunner, H.1    Obermann, U.2
  • 38
    • 0033999757 scopus 로고    scopus 로고
    • Transfer hydrogenation and oxazaborolidine-catalyzed reduction of ketones with borane have been shown to proceed through a six-membered transition state : a) M. Yamakawa, H. Ito, R. Noyori, J. Am. Chem. Soc. 2000, 122, 1466;
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 1466
    • Yamakawa, M.1    Ito, H.2    Noyori, R.3
  • 40
    • 33746364092 scopus 로고    scopus 로고
    • note
    • Replacing the Ph in 6 with tBu led to virtually identical results, which rules out arene-arene interactions of the substrate with the Ph in 6.
  • 44
    • 23944460499 scopus 로고    scopus 로고
    • Birman et al. recently invoked arene-arene interactions to rationalize the kinetic resolution in the acylation of racemic alcohols: b) V. B. Birman, H. Jiang, Org. Lett. 2005, 7, 3445.
    • (2005) Org. Lett. , vol.7 , pp. 3445
    • Birman, V.B.1    Jiang, H.2
  • 45
    • 4243539377 scopus 로고
    • The geometries of monomers were determined by the cc-pVTZ/ RI-MP2 gradient optimization in the Turbomole v.5.6 package (R. Ahlrichs, M. Bär, M. Häser, H. Horn, C. Kölmel, Chem. Phys. Lett. 1989, 162, 165); the optimized geometries of monomers were kept frozen throughout the scans. Interaction energies were computed with aug-cc-pVDZ basis set at RI-MP2 level in Turbomole v.5.6 and are BSSE-corrected. Only the face-to-face geometry was examined, thus keeping the planes of the monomers parallel throughout the scans.
    • (1989) Chem. Phys. Lett. , vol.162 , pp. 165
    • Ahlrichs, R.1    Bär, M.2    Häser, M.3    Horn, H.4    Kölmel, C.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.