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Volumn 128, Issue 36, 2006, Pages 11776-11777

Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution

Author keywords

[No Author keywords available]

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; LANTHANUM; LITHIUM; METAL COMPLEX; NITRO DERIVATIVE; NITROALDOL DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33748496246     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja064858l     Document Type: Article
Times cited : (111)

References (33)
  • 8
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    • One example using 2,2,2-trifluoroacetophenone to give the product with low ee (21% ee) was reported. Misumi, Y.; Bulman, R. A.; Matsumoto, K. Heterocycles 2002, 56, 599.
    • (2002) Heterocycles , vol.56 , pp. 599
    • Misumi, Y.1    Bulman, R.A.2    Matsumoto, K.3
  • 12
    • 0030788440 scopus 로고    scopus 로고
    • For asymmetric nitroaldol reaction of aldehydes using LLB 2a, see review: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236. For other examples of catalytic asymmetric nitroaldol reactions of aldehydes, see ref 1.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 1236
    • Shibasaki, M.1    Sasai, H.2    Arai, T.3
  • 13
    • 33748516010 scopus 로고    scopus 로고
    • note
    • -1.
  • 16
    • 33748515077 scopus 로고    scopus 로고
    • note
    • (R)-LLB 2a also promoted nitroaldol reactions of other simple ketones in high enantioselectivity, albeit in poor yields. Ketone 3d (90% ee, 5% yield); 3e (89% ee, 20% yield).
  • 19
  • 20
    • 33646121294 scopus 로고    scopus 로고
    • and references therein
    • For examples of nonenzymatic kinetic resolution of tert-alcohols, see: (b) Angione, M. C.; Miller, S. J. Tetrahedron 2006, 62, 5254 and references therein.
    • (2006) Tetrahedron , vol.62 , pp. 5254
    • Angione, M.C.1    Miller, S.J.2
  • 21
    • 33748510031 scopus 로고    scopus 로고
    • note
    • The absolute configurations of 4a, 4e, and 4f were determined to be R after conversion into known compounds. See Supporting Information.
  • 22
    • 0002178750 scopus 로고    scopus 로고
    • The s values in this paper were calculated based on conversion and ee of recovered 4 assuming first-order kinetic dependence on 4. Kinetic studies are required to determine accurate s values. For discussion on the validity of calculated s values, see: Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5. See also ref 9a.
    • (2001) Adv. Synth. Catal. , vol.343 , pp. 5
    • Keith, J.M.1    Larrow, J.F.2    Jacobsen, E.N.3
  • 29
    • 33748492405 scopus 로고    scopus 로고
    • note
    • Because the known synthetic methods of racemic tertiary nitroaldols did not afford satisfactory yield for 4f, we developed a new synthetic method. See Supporting Information for details.
  • 30
    • 4744353743 scopus 로고    scopus 로고
    • Ligand liability of related rare earth-alkali metal heterobimetallic complexes was reported. (a) Bari, L. D.; Lelli, M.; Salvadori, P. Chem.-Eur. J. 2004, 10, 4594.
    • (2004) Chem.-Eur. J. , vol.10 , pp. 4594
    • Bari, L.D.1    Lelli, M.2    Salvadori, P.3
  • 32
    • 33748510253 scopus 로고    scopus 로고
    • note
    • For full details of ESI-MS data [m/z 200-1300] of LLB 2a, LLB* 2b, 2a/2b = 2:1. and 2a/2b = 1:2, see Supporting Information. Although it is impossible to discuss quantitatively using MS, we believe the ESI-MS data at least suggested the presence of mixed-ligand La-Li complexes in the mixture of LLB 2a and LLB* 2b. NMR analysis only resulted in a complex mixture spectrum.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.