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Volumn 15, Issue 3, 2004, Pages 481-488

Kinetic resolution of (±)-trans- and (±)-cis-2- phenylcyclopentanamine by CALB-catalyzed aminolysis of esters: The key role of the leaving group

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYLCYCLOPENTANAMINE; ACETIC ACID DERIVATIVE; ACETIC ACID ETHYL ESTER; AMINE; CYCLOPENTANE DERIVATIVE; ESTER; FUNGAL ENZYME; LIPASE B; PHENETHYL ALCOHOL; UNCLASSIFIED DRUG;

EID: 0742289584     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.11.013     Document Type: Article
Times cited : (42)

References (42)
  • 25
    • 0032552502 scopus 로고    scopus 로고
    • In a kinetic study, we had demonstrated that tert-butylmethyl ether is the solvent in which CALB exhibits a higher catalytic activity:
    • In a kinetic study, we had demonstrated that tert-butylmethyl ether is the solvent in which CALB exhibits a higher catalytic activity: García-Alles L.F., Gotor V. Biotechnol. Bioeng. 59:1998;684-694.
    • (1998) Biotechnol. Bioeng. , vol.59 , pp. 684-694
    • García-Alles, L.F.1    Gotor, V.2
  • 26
    • 85030907274 scopus 로고    scopus 로고
    • note
    • tOMe was used, a side CALB-catalyzed hydrolysis of the acyl donor 12 took place. Thus, the resulting (R)-1-phenylethanol arose from aminolysis and hydrolysis of (±)-12 . For this reason, enantiomeric ratio for the acyl donor was not determined. Nevertheless, the high ee (92%) obtained for the alcohol reveals that the (S)-enantiomer of the acyl donor (S)-12 was almost unreacted.
  • 28
    • 0027509450 scopus 로고
    • (±)-1-Phenylethanol was previously resolved with CALB using S-ethyl thiooctanoate ( E>200 ):
    • (±)-1-Phenylethanol was previously resolved with CALB using S-ethyl thiooctanoate ( E>200 ): Frykman H., Öhrner N., Norin T., Hult K. Tetrahedron Lett. 34:1993;1367-1370.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 1367-1370
    • Frykman, H.1    Öhrner, N.2    Norin, T.3    Hult, K.4
  • 29
    • 84987189531 scopus 로고
    • (±)-trans-2-Phenylcyclopentanol was previously resolved ( E>100 ) with a lipase derived from Pseudomonas sp (SAM II) under similar reaction conditions:
    • (±)-trans-2-Phenylcyclopentanol was previously resolved ( E>100 ) with a lipase derived from Pseudomonas sp (SAM II) under similar reaction conditions: Seemayer R., Schneider M.P. Recl. Trav. Chim. Pays-Bas. 110:1991;171-174.
    • (1991) Recl. Trav. Chim. Pays-Bas , vol.110 , pp. 171-174
    • Seemayer, R.1    Schneider, M.P.2
  • 30
    • 85030910221 scopus 로고    scopus 로고
    • note
    • Enzyme-catalyzed kinetic resolution of (±)-21 has not been reported. Synthesis of (±)-21 was carried out from (±)-20 by Mitsunobu reaction with p -nitrobenzoic acid and subsequent hydrolysis of the resulting (±)-cis-2-phenylcyclopentyl p -nitrobenzoate.
  • 31
    • 85030900403 scopus 로고    scopus 로고
    • note
    • Similarly, (R)-1-phenylethanol was isolated with 92% and 93% ee from reaction of (±)-2 with (±)-12 and (±)-14 , respectively. (1R,2S)-trans-2-Phenylcyclopentanol with 99% ee was obtained from the analogous reaction with (±)-15.
  • 33
  • 39
    • 26144443400 scopus 로고    scopus 로고
    • Fluka catalog, , p 1128.
    • (2002) Fluka catalog , pp. 1128


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.