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Volumn 15, Issue 38, 2009, Pages 9911-9917

Asymmetrie [2,3]-wittig rearrangement of oxygenated allyI benzyl ethers in the presence of a chiral di-tBu-bis(oxazoline) ligand: A novel synthetic approach to THF lignans

Author keywords

External chiral ligands; Lignans; Stereoselectivity; Wittig rearrangement asymmetric synthesis

Indexed keywords

ASYMMETRIC SYNTHESIS; BENZYL ETHERS; BENZYL GROUP; BENZYLIC; CATALYTIC AMOUNTS; CHIRAL LIGAND; DIASTEREO- AND ENANTIOSELECTIVITY; ENANTIOSELECTIVE; FUNCTIONALIZED; HIGH ENANTIOSELECTIVITY; LIGNANS; METHOXY; OXAZOLINES; PHENYL SUBSTITUENTS; SYNTHETIC APPROACH; WITTIG REARRANGEMENT;

EID: 70450162319     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901212     Document Type: Article
Times cited : (27)

References (36)
  • 10
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    • Eds.: B. M. Trost, I. Fleming, Pergamon, New York
    • e) J. A. Marshall, in Com- prehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, Vol.3, pp. 975-1014.
    • (1991) Com- Prehensive Organic Synthesis , vol.3 , pp. 975-1014
    • Marshall, J.A.1
  • 27
    • 70450137172 scopus 로고    scopus 로고
    • The optical purities of 12a and 12b were not determined
    • The optical purities of 12a and 12b were not determined.
  • 31
    • 70450120013 scopus 로고
    • Isobe and co-workers reported that some a-aromatic secondary alcohols show irregular Δδ values for the β-protons in the modified Mosher method, presumably due to the anisotropic effects of the aaromatic groups. They also reported that these irregular data can be neglected for determination of the absolute configuration by the modified Mosher method. Some of our [2,3]-Wittig products also exhibited the same irregular Δδ values for the β-protons and the absolute configurations were assigned according to Isobe's report; see I. Ohtani, K. Hotta, Y Ichikawa, M. Isobe, Chem. Lett. 1995, 513-514.
    • (1995) Chem. Lett. , pp. 513-514
    • Hotta, K.1    Ichikawa, Y.2    Isobe, M.3
  • 32
    • 70450132227 scopus 로고    scopus 로고
    • In dilute conditions, the ee of the alcohol 7d was improved to 59% ee but with a reduction in the yield to 19%. The Mosher ester was prepared from 7d with moderate optical purity
    • In dilute conditions, the ee of the alcohol 7d was improved to 59% ee but with a reduction in the yield to 19%. The Mosher ester was prepared from 7d with moderate optical purity.
  • 34
    • 34250722048 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 4514-4518.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 4514-4518
  • 35
    • 70450157499 scopus 로고    scopus 로고
    • The absolute configuration of 7k was determined by the modified Mosher method
    • The absolute configuration of 7k was determined by the modified Mosher method.
  • 36
    • 70450157500 scopus 로고    scopus 로고
    • The absolute configuration of the major enantiomer of 7 a was confirmed by chiral HPLC; that of 7j was not determined
    • The absolute configuration of the major enantiomer of 7 a was confirmed by chiral HPLC; that of 7j was not determined.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.