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Volumn 1, Issue 6, 1999, Pages 841-843

A chiral rhodium complex for rapid asymmetric transfer hydrogenation of imines with high enantioselectivity

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; IMINE; RHODIUM;

EID: 0033598249     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990098q     Document Type: Article
Times cited : (232)

References (42)
  • 8
  • 24
    • 85034149463 scopus 로고    scopus 로고
    • note
    • The catalyst was pentamethylcyclopentadienylrhodium chloride dimer from Aldrich Chemical Co. (catalog no. 33,837-0).
  • 25
    • 85034132908 scopus 로고    scopus 로고
    • Abstracts of papers
    • Anaheim, CA, March 21-25, American Chemical Society: Washington, DC, 1999, ORGN 279
    • Mao, Jianmin; Baker, D. C. Abstracts of Papers, 217th National Meeting of the American Chemical Society, Anaheim, CA, March 21-25, 1999; American Chemical Society: Washington, DC, 1999, ORGN 279.
    • (1999) 217th National Meeting of the American Chemical Society
    • Mao, J.1    Baker, D.C.2
  • 26
    • 85034137173 scopus 로고    scopus 로고
    • note
    • 1e,2e that an NH moiety in the ligand may promote stabilization of the requisite cyclic transition state through hydrogen bonding to the substrate. This type of metal-ligand bifunctional catalyst may increase the ability of the substrate to bind the active site of the catalyst, thereby increasing reactivity and selectivity.
  • 30
    • 0003038913 scopus 로고    scopus 로고
    • After our work had been carried out, the catalyst described herein has been advanced for the transfer hydrogenation of carbonyl compounds. See: Mashina, K.; Abe, T.; Tani, K. Chem. Lett. 1998, 1199-1200, 1201-1202. Kunikiko, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186-2187. We find that 1 is more successful in reducing imines than ketones as evidenced by higher yields of products with generally excellent enantioselectivity.
    • (1998) Chem. Lett. , vol.1199-1200 , pp. 1201-1202
    • Mashina, K.1    Abe, T.2    Tani, K.3
  • 31
    • 0033515561 scopus 로고    scopus 로고
    • After our work had been carried out, the catalyst described herein has been advanced for the transfer hydrogenation of carbonyl compounds. See: Mashina, K.; Abe, T.; Tani, K. Chem. Lett. 1998, 1199-1200, 1201-1202. Kunikiko, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186-2187. We find that 1 is more successful in reducing imines than ketones as evidenced by higher yields of products with generally excellent enantioselectivity.
    • (1999) J. Org. Chem. , vol.64 , pp. 2186-2187
    • Kunikiko, K.1    Ikariya, T.2    Noyori, R.3
  • 34
    • 85034137713 scopus 로고    scopus 로고
    • note
    • 2RhS: C, 58.26; H, 5.68; Cl, 5.55; N, 4.38; S, 5.02; Found: C, 58.18; H, 5.67; Cl, 5.69; N, 4.29; S, 4.92.
  • 36
    • 85034140271 scopus 로고    scopus 로고
    • note
    • 2e for 6d, see Table 1, last two entries.
  • 41
    • 85034149580 scopus 로고    scopus 로고
    • note
    • Baker, D. C., and co-workers, unpublished work. Details on the synthesis and structural identification of 7d will be reported in the full paper.
  • 42
    • 85034155558 scopus 로고    scopus 로고
    • note
    • The absolute configuration was confirmed by single-crystal X-ray diffraction carried out on the N-Me derivative of 7d.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.