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Volumn 62, Issue 26, 2006, Pages 6303-6311

Asymmetric syntheses of N-substituted α-amino esters via dynamic kinetic resolution of α-haloacyl diacetone-d-glucose

Author keywords

Asymmetric syntheses; Carbohydrate; Chiral auxiliary; Dynamic kinetic resolution; Nucleophilic substitution

Indexed keywords

1,1' IMINODICARBOXYLIC ACID DERIVATIVE; ALLOSE; ALPHA AMINO ESTER DERIVATIVE; ALPHA HALO ESTER DERIVATIVE; ALPHA HALOACYL DIACETONE DEXTRO GLUCOSE; AMINE; AMINE NUCLEOPHILE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; ETHYLDIISOPROPYLAMINE; GLUCOSE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

EID: 33646758906     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.04.045     Document Type: Article
Times cited : (24)

References (51)
  • 11
    • 33646787682 scopus 로고    scopus 로고
    • For reviews on carbohydrate chiral auxiliary, see:
  • 28
    • 33646756061 scopus 로고    scopus 로고
    • For reviews on carbohydrate chiral ligand, see:
  • 37
    • 33646771217 scopus 로고    scopus 로고
    • note
    • 1H NMR, which can rule out the possibility of epimerization after the nucleophilic substitution reaction.
  • 38
    • 33646757099 scopus 로고    scopus 로고
    • When we prepared diacetone-d-glucose bound α-halo esters from racemic α-halo carboxylic acid derivatives, we obtained 5 and 6 with 69:31 dr and 73:27 dr, respectively. Formation of anything other than a 1:1 mixture of diastereomers can be explained by dynamic resolution of α-halo acids in the ester bond formation with chiral auxiliary. Alternatively, the in situ preparation of a ketene from α-halo acid halides and its treatment with a chiral auxiliary can afford diastereomerically enriched α-halo esters. For examples, see:
  • 41
    • 1042275590 scopus 로고    scopus 로고
    • The 55:45 diastereomeric mixture of 6 is prepared by column chromatography with fractional collection
    • Cardillo G., Fabbroni S., Gentilucci L., Perciaccante R., and Tolomelli A. Tetrahedron: Asymmetry 15 (2004) 593 The 55:45 diastereomeric mixture of 6 is prepared by column chromatography with fractional collection
    • (2004) Tetrahedron: Asymmetry , vol.15 , pp. 593
    • Cardillo, G.1    Fabbroni, S.2    Gentilucci, L.3    Perciaccante, R.4    Tolomelli, A.5
  • 42
    • 33646789012 scopus 로고    scopus 로고
    • note
    • When nucleophiles such as tritylthiol, sodium malonate, sodium 3,5-dimethoxyphenoxides, and potassium 6-flavonoxide were used for the reaction with 1 or 2, the corresponding substitution products were obtained in 76-94% yields with diastereomeric ratios from 69:31 to 54:46.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.