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Volumn 75, Issue 21, 2010, Pages 7365-7372

Enantioselective synthesis of α-fluoro-β3-amino esters: Synthesis of enantiopure, orthogonally protected α-fluoro- β3-lysine

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ESTERS; CHIRAL POOL; CONJUGATE ADDITION; ENANTIOPURE; ENANTIOSELECTIVE SYNTHESIS; FLUORINATING AGENTS; LITHIUM AMIDE; QUANTITATIVE YIELDS; SIDE CHAINS; UNSATURATED ESTERS;

EID: 78049492526     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101600c     Document Type: Article
Times cited : (23)

References (33)
  • 20
    • 78049489875 scopus 로고    scopus 로고
    • The yields shown for the second and third steps in Scheme 2 result from optimization performed after the publication of ref 11. Ph.D. Dissertation, Monash University, Clayton, Victoria, Australia
    • The yields shown for the second and third steps in Scheme 2 result from optimization performed after the publication of ref 11. Bromfield, K. M. Ph.D. Dissertation, Monash University, Clayton, Victoria, Australia, 2005.
    • (2005)
    • Bromfield, K.M.1
  • 21
    • 78049492642 scopus 로고    scopus 로고
    • A preliminary report (11) describes a reaction similar to the one that produced 5a from the crotonate 1a, but in the previous study, the experiment was performed with the corresponding ethyl ester. While the dr's obtained with the ethyl and tert -butyl esters were very similar, the yield was much lower for the ethyl ester (39%), presumably as a result of competing 1,2-addition of the lithium amide 2. The use of the bulkier tert -butyl ester is known to limit this undesired side reaction. (10)
    • A preliminary report (11) describes a reaction similar to the one that produced 5a from the crotonate 1a, but in the previous study, the experiment was performed with the corresponding ethyl ester. While the dr's obtained with the ethyl and tert -butyl esters were very similar, the yield was much lower for the ethyl ester (39%), presumably as a result of competing 1,2-addition of the lithium amide 2. The use of the bulkier tert -butyl ester is known to limit this undesired side reaction. (10)
  • 28
    • 78049487945 scopus 로고    scopus 로고
    • 19th International Symposium on Fluorine Chemistry, Jackson Hole, WY,; Abstract 160, p
    • March, T. L.; Johnston, M. R.; Duggan, P. J. Book of Abstracts, 19th International Symposium on Fluorine Chemistry, Jackson Hole, WY, 2009; Abstract 160, p 87.
    • (2009) Book of Abstracts , pp. 87
    • March, T.L.1    Johnston, M.R.2    Duggan, P.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.