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Volumn , Issue 6, 2000, Pages 784-788

An efficient method for the preparation of enantiomerically pure N- acylarylsulfonamides having an asymmetric center at the α-position: Condensation of acid chlorides and arylsulfonamides under solid-liquid two- phase conditions

Author keywords

Chiral N acylarylsulfonamides; Chiral phenylacetic acid; Powdered alkaline hydroxide; Racemization; Solid liquid two phase conditions

Indexed keywords

CARBONYL DERIVATIVE; CHLORIDE; PHENYLACETIC ACID; SULFONAMIDE;

EID: 0034125979     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6270     Document Type: Article
Times cited : (32)

References (27)
  • 9
    • 0343788673 scopus 로고
    • Jpn, Kokai Tokkyo Koho. JP 06172323
    • Go, A.; Kudo, S.; Takahashi, T.; Higure, R. Jpn, Kokai Tokkyo Koho. JP 06172323, 1994; Chem. Abstr. 1995, 122, 133207.
    • (1994) Chem. Abstr. , vol.122 , pp. 133207
    • Go, A.1    Kudo, S.2    Takahashi, T.3    Higure, R.4
  • 17
    • 0342483493 scopus 로고    scopus 로고
    • note
    • The optical purity of (R)-2a was determined as (R)-1a by quenching with water. We estimated the optical purity of (R)-2a to be approximately 98%ee at this stage.
  • 19
    • 0010016728 scopus 로고
    • Ketene, their cumulene analogues and their S, Se and Te analogue
    • Pattenden, G., Ed.; Pergamon: Oxford
    • (b) Harrowven, D. C.; Dennison, S. T. Ketene, Their Cumulene Analogues and Their S, Se and Te Analogue. In Comprehensive Organic Functional Group Transformations, Vol. 3; Pattenden, G., Ed.; Pergamon: Oxford, 1995, p 525.
    • (1995) Comprehensive Organic Functional Group Transformations , vol.3 , pp. 525
    • Harrowven, D.C.1    Dennison, S.T.2
  • 20
    • 0343788647 scopus 로고    scopus 로고
    • note
    • Commercially available potassium hydroxide contains 12.1% (w/w) of water, which correspond to 1.5 equivalents of (R)-2a in Entry 8 (see experimental).
  • 23
    • 0342483487 scopus 로고    scopus 로고
    • note
    • A catalytic amount of DMF was added for the preparation of 2b-d.
  • 24
    • 0342483486 scopus 로고    scopus 로고
    • note
    • In the stepwise method for the preparation of 4b-d, 2.2 equivalents of powdered KOH was used while 3.3 equivalents of base was required in the one-pot method.
  • 25
    • 0343352908 scopus 로고    scopus 로고
    • note
    • The absolute configurations of (R)-1a and (R)-4a were determined by X-ray crystallographic analysis as their diastereomeric salts with ehiral amines, which will be reported elsewhere.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.