메뉴 건너뛰기




Volumn 71, Issue 14, 2006, Pages 5377-5379

Practical synthesis of an L-fructose-derived ketone catalyst for asymmetric epoxidation of olefins

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDATION; L-FRUCTOSE-DERIVED KETONE; L-SORBOSE; TRI SUBSTITUTED OLEFINS;

EID: 33745700292     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060335k     Document Type: Article
Times cited : (63)

References (22)
  • 1
    • 0032975651 scopus 로고    scopus 로고
    • For reviews on chiral ketone-catalyzed asymmetric epoxidation, see: (a) Denmark, S. E.; Wu, Z. Synlett 1999, 847.
    • (1999) Synlett , pp. 847
    • Denmark, S.E.1    Wu, Z.2
  • 10
    • 0035906456 scopus 로고    scopus 로고
    • For a stepwise synthesis of L-fructose from L-sorbose, see: Bach, T.; Hofer, F. J. Org. Chem. 2001, 66, 3427.
    • (2001) J. Org. Chem. , vol.66 , pp. 3427
    • Bach, T.1    Hofer, F.2
  • 15
    • 33745694586 scopus 로고    scopus 로고
    • note
    • 4 per gram of substrate) was found to work well. A prolonged reaction time could also lead to the decomposition of the compound.
  • 16
    • 33745694585 scopus 로고    scopus 로고
    • note
    • Although a higher concentration of base can accelerate the reaction, the reaction mixture becomes complex. Considering the reaction efficiency and stability of the product, using 9 M NaOH and refluxing for 8 h worked well.
  • 17
    • 33745694589 scopus 로고    scopus 로고
    • note
    • The reaction should be carefully monitored by TLC and quenched as soon as the reaction is finished. Heating the reaction mixture for a long time causes problems, possibly polymerization of the L-fructose.
  • 18
    • 33745694588 scopus 로고    scopus 로고
    • note
    • Large quantities of L-sorbose were purchased from MP Biomedicals, LLC (Aurora, OH).
  • 19
    • 33745722809 scopus 로고    scopus 로고
    • note
    • The GC retention time of the main peak is 3.32 min. Conditions: column, VA-5MS, Varian chromatography systems (VA-122553-20); oven, from 150 to 250°C (20°C/min); carrier, helium, head pressure 25 psi; detection: FID 250°C.
  • 20
    • 33745694580 scopus 로고    scopus 로고
    • note
    • f/values of compounds 4, 5, and 6 are 0.57, 0.70, and 0.30, respectively, using EtOAc as a solvent.
  • 21
    • 33745708669 scopus 로고    scopus 로고
    • note
    • The obtained L-fructose was a sticky syrup. Freezing the syrup with dry ice led to a solid which was easier to manipulate.
  • 22
    • 33745680379 scopus 로고    scopus 로고
    • note
    • Alcohol 7 is the kinetic product of the reaction. Controlling the reaction time is important to minimize its isomerization to the thermodynamic product. The GC retention time of the main peak is 4.42 min. Conditions: column, VA-5MS, Varian chromatography systems (VA-122553-20); oven, 170°C; carrier, helium, head pressure 25 psi; detection, FID 250°C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.