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Volumn , Issue 7, 2009, Pages 1136-1140

Synthesis of highly functionalized proline derivatives via a one-pot Michael/aldol addition-cyclization approach

Author keywords

Aldol reaction; Amino acids; Chelates; Cyclization; Michael addition; One pot reaction

Indexed keywords

ALDEHYDE; ALPHA BETA UNSATURATED ESTER; CHELATE; CHELATED ENOLATE DERIVATIVE; ESTER DERIVATIVE; PROLINE; UNCLASSIFIED DRUG;

EID: 67649388100     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1088150     Document Type: Article
Times cited : (9)

References (43)
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    • note
    • In some cases the reactions of chelated enolates with aromatic aldehydes proceed with low diastereoselectivicity, probably because of the reversibility of the aldol process.
  • 36
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    • No epimerization of the ester 7a was observed. According to Seebach et al. LHMDS is not able to deprotonate amino acid esters except glycine and sarcosine, see: Ernst, B.; Leumann, C., Eds.; Verlag Helvetica Chimica Acta: Basel, and references cited therein
    • No epimerization of the ester 7a was observed. According to Seebach et al. LHMDS is not able to deprotonate amino acid esters except glycine and sarcosine, see: Seebach, D.; Beck, A. K.; Studer, A. In Modern Synthetic Methods, Vol.7; Ernst, B.; Leumann, C., Eds.; Verlag Helvetica Chimica Acta: Basel, 1995, 1-178; and references cited therein.
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    • Seebach, D.1    Beck, A.K.2    Studer, A.3
  • 37
    • 67649405120 scopus 로고    scopus 로고
    • note
    • It should be mentioned, that NMR is not a suitable method for determination of the isomeric ratios, because in addition to the signals of the different isomers, in general a double set of signals is observed caused by rotamers (hindered rotation around the secondary amide bond).
  • 41
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    • note
    • 2, hexanes-EtOAc).
  • 42
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    • note
    • 6 (397.39): C, 51.38; H, 6.56; N, 3.52. Found: C, 50.98; H, 6.37; N, 3.56.
  • 43
    • 67649402242 scopus 로고    scopus 로고
    • note
    • Unfortunately the aldol products obtained with aromatic aldehydes could not be analyzed by GC; NMR has to be used in this case. Therefore, we were not able to determine exact ratios, but the NMR spectra indicated that the isomers were formed in comparable amounts.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.