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Volumn 8, Issue 18, 2010, Pages 4165-4168

Switching from (R)- to (S)-selective chemoenzymatic DKR of amines involving sulfanyl radical-mediated racemization

Author keywords

[No Author keywords available]

Indexed keywords

DYNAMIC KINETIC RESOLUTION; ENANTIOMERIC EXCESS; GOOD YIELD; SULFANYL RADICALS; SWITCHABLE;

EID: 77955934426     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00054j     Document Type: Article
Times cited : (34)

References (42)
  • 3
    • 0035632503 scopus 로고    scopus 로고
    • For selected reviews dealing with the synthesis of chiral amines, see:
    • G. Hieber K. Ditrich Chim. Oggi 2001 19 16
    • (2001) Chim. Oggi , vol.19 , pp. 16
    • Hieber, G.1    Ditrich, K.2
  • 24
    • 0001079960 scopus 로고    scopus 로고
    • For preliminary reports on amines racemization, see:
    • M. T. Reetz K. Schimossek Chimia 1996 50 668
    • (1996) Chimia , vol.50 , pp. 668
    • Reetz, M.T.1    Schimossek, K.2
  • 34
    • 63349102356 scopus 로고    scopus 로고
    • and refs cited therein
    • F. Bordera Chem. Rev. 2002 102 4817
    • (2002) Chem. Rev. , vol.102 , pp. 4817
    • Bordera, F.1
  • 40
    • 40949160930 scopus 로고    scopus 로고
    • The rate slow-down was assigned to the solvation of the amine by hydrogen bonding that would increase the α-CH BDE. For the incidence of intramolecular hydrogen bonding on the α-CH BDE in amines, see:
    • L. Routaboul N. Vanthuyne S. Gastaldi G. Gil M. P. Bertrand J. Org. Chem. 2008 73 364
    • (2008) J. Org. Chem. , vol.73 , pp. 364
    • Routaboul, L.1    Vanthuyne, N.2    Gastaldi, S.3    Gil, G.4    Bertrand, M.P.5
  • 42
    • 20644469267 scopus 로고
    • Only the natural S-isomer is recognized by the enzyme, therefore the racemic acyl donor can be used without changing the result but the quantity has to be doubled This happened to be the case for 1-phenyl-2-amino-propane
    • C. S. Chen Y. Fujimoto C. J. Girdaukas C. J. Sih J. Am. Chem. Soc. 1982 104 7294
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 7294
    • Chen, C.S.1    Fujimoto, Y.2    Girdaukas, C.J.3    Sih, C.J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.