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Volumn , Issue 8, 2003, Pages 1181-1186

Development of new chiral auxiliary derived from (S)-(-)-phenylethylamine for a synthesis of enantiopure (R)-2-propyloctanoic acid

Author keywords

Asymmetric synthesis; Chiral auxiliary; Crystallinity; (1S) 1 phenylethyl amino phenol, (R) 2 propyloctanoic acid

Indexed keywords

CRYSTALLINE MATERIALS; PHENOLS; SYNTHESIS (CHEMICAL);

EID: 0038726096     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39394     Document Type: Article
Times cited : (18)

References (39)
  • 1
    • 0038418837 scopus 로고    scopus 로고
    • Current address: Department of Chemistry, University of Chicago, 5735 South Ellis Avenue.Chicago, IL 60637, USA
    • Current address: Department of Chemistry, University of Chicago, 5735 South Ellis Avenue.Chicago, IL 60637, USA.
  • 3
    • 53149132849 scopus 로고
    • (a) Ohuchida, S.; Kishimoto, K.; Tateishi, N.; Ohno, H. EP 632008, 1995; Chem. Abstr. 1995, 122, 160096.
    • (1995) Chem. Abstr. , vol.122 , pp. 160096
  • 17
    • 0037742747 scopus 로고    scopus 로고
    • See Ref
    • See Ref.
  • 19
    • 0038080275 scopus 로고    scopus 로고
    • (b) For aldol reaction using a N-tosyl derivative with high diastereoselectivity, see: Hirai, K.; Maruyama, H. J. Synth. Org. Chem. Jpn. 1999, 5, 382.
    • (1999) J. Synth. Org. Chem. Jpn. , vol.5 , pp. 382
    • Hirai, K.1    Maruyama, H.2
  • 23
    • 0038080274 scopus 로고    scopus 로고
    • note
    • 4 (3 equiv), THF, 73%, 80%].
  • 24
    • 0037742748 scopus 로고    scopus 로고
    • note
    • The absolute configuration of the product was determined after conversion to the carboxylic acid 1. See Ref.
  • 32
    • 0038418835 scopus 로고    scopus 로고
    • note
    • The Cerius-2 version 4.0 software package (Accerlys Inc., San Diego, CA.) was used for the conformational analysis. The systematic conformation search was performed utilizing the UNIVERSAL 1.02 force field, which possesses the parameters for lithium atom. A dielectric constant of 8.20 was used to simulate the THF solvent. Two dihedral angles, which construct the enolate face was fixed at 0° or 180°, and the remaining five dihedral angles were varied systematically at 30° steps. Each conformer was energy-minimized, and conformation energy was evaluated.
  • 36
    • 0038080270 scopus 로고
    • Tsvetkov, E. N.; Syundyukova, V. K.; Baulin, V. E. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 147; Chem. Abstr. 1990, 112, 566055.
    • (1990) Chem. Abstr. , vol.112 , pp. 566055


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.