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Volumn 66, Issue 40, 2010, Pages 8076-8088

The stereodivergent asymmetric synthesis of a range of 2-(1′- hydroxyalkyl)phenols

Author keywords

Arene chromium tricarbonyl; Asymmetric synthesis; Enantiopure carbinols; Stereoselective deprotonation

Indexed keywords

BENZYL ALCOHOL; GRIGNARD REAGENT; PHENOL DERIVATIVE;

EID: 77956392550     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.07.058     Document Type: Article
Times cited : (8)

References (49)
  • 33
    • 0036435540 scopus 로고    scopus 로고
    • We have previously employed mutual kinetic resolution protocols to assay the level of enantiorecognition between two racemic species, see: S. Bailey, S.G. Davies, A.D. Smith, and J.M. Withey Chem. Commun. 2002 2910
    • (2002) Chem. Commun. , pp. 2910
    • Bailey, S.1    Davies, S.G.2    Smith, A.D.3    Withey, J.M.4
  • 40
    • 77956392417 scopus 로고    scopus 로고
    • 3 complexed arenes.
    • 3 complexed arenes.
  • 43
    • 77956395085 scopus 로고    scopus 로고
    • note
    • The fact that 26 and 27 were produced as single diastereoisomers (>99:1 dr) suggests that upon diastereoselective deprotonation and subsequent methylation of (S)-3 an epimerisation process is occurring to give 7 in 95:5 dr.
  • 44
    • 77956392306 scopus 로고    scopus 로고
    • note
    • -l) suggests that the carbonyl group of the tert-butyl ketone is not able to adopt a geometry which is coplanar with the complexed aryl ring due to unfavourable steric interactions.
  • 46
    • 0002096987 scopus 로고
    • It has previously been reported that benzyl ethers are cleaved faster than benzyl alcohols via hydrogenolysis, see: A.P.G. Kieboom, J.F. de Kreuk, and H. van Bekkum J. Catal. 20 1971 58
    • (1971) J. Catal. , vol.20 , pp. 58
    • Kieboom, A.P.G.1    De Kreuk, J.F.2    Van Bekkum, H.3
  • 47
    • 77956394345 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopic analysis in the presence of (R)-(-)-l-(9-anthry1)-2,2,2-trifluoroethanol as the chiral solvating agent, upon comparison with authentic racemic samples.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.