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Volumn 9, Issue 11, 1998, Pages 1843-1846

A convenient resolution of long-chain alkyl epoxides with Jacobsen's salen(Co)III(OAc) catalysts

Author keywords

Asymmetric reactions; Enantiomeric purity; Epoxides; Resolution

Indexed keywords

ALKENE; EPOXIDE;

EID: 0032486157     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00175-X     Document Type: Article
Times cited : (59)

References (37)
  • 12
    • 0010421516 scopus 로고    scopus 로고
    • note
    • 12. In our hands, the following reactions produced moderate to poor results: Sharpless asymmetric epoxidation and asymmetric dihydroxylation of 1-heptadecene (ee<80%); lipase PS-30 catalyzed acetylation of 1-bromo-2-hydroxyhexa-and octadecane (ee<60%); chiral reduction of 1-bromooctadecan-2-one with DIP-Cl (ee<20%). Attachment of a long chain to an enantiopure glycerol equivalent via nucleophilic displacement gave no or low yield of the desired products. The literature contains many examples of Wittig homologation of glyceraldehyde derived from D-mannitol and L-ascorbic acid to introduce a long chain.
  • 29
    • 0010419954 scopus 로고
    • 3 by oxidation of eicosene with 3-chloroperoxybenzoic acid in 87% yield (Muzart, J.; Riahi, A. J. Organomet. Chem. 1992, 433, 323-336).
    • (1992) J. Organomet. Chem. , vol.433 , pp. 323-336
    • Muzart, J.1    Riahi, A.2
  • 30
    • 0010421371 scopus 로고    scopus 로고
    • note
    • 30. Catalysts (Aldrich Chemical Co. catalogue numbers for R,R-: 47,459-2 and for S,S-: 47,460-6) were used as received.
  • 31
    • 0010420952 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra. (R)-and (5)-2-Tetradecyl-, -2-hexadecyl-, and -2-octadecyloxiranes were isolated as low melting waxy solids, mp <36 EC.
  • 33
    • 0010503237 scopus 로고    scopus 로고
    • note
    • 31
  • 35
    • 0010501273 scopus 로고    scopus 로고
    • note
    • 19F NMR -72.67.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.