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Volumn 70, Issue 10, 2005, Pages 4162-4165

Addition of Cl2C: To (-)-O-menthyl acrylate under sonication-phase-transfer catalysis. Efficient synthesis of (+)- and (-)-(2-chlorocyclopropyl)methanol

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CRYSTALLIZATION; ESTERS; ISOMERS; METHANOL; PHASE TRANSITIONS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS;

EID: 18744394940     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0480186     Document Type: Article
Times cited : (24)

References (17)
  • 4
    • 18744402833 scopus 로고    scopus 로고
    • note
    • 3 and 50% w/v aq NaOH contained in a heavy glass pressure vessel at elevated temperature (∼100-120 °C) led to an explosive failure of the glass vessel. We surmised the cause was either excessive solvent vapor pressure or an unidentified exotherm ("runaway" reaction).
  • 7
    • 18744387049 scopus 로고    scopus 로고
    • note
    • D ∼ 1.7) may be underestimated in these experiments.
  • 11
    • 0034649726 scopus 로고    scopus 로고
    • (b) Olivo, H. F.; Velaquez, F.; Trevisan, H. C. Org. Lett. 2000, 2, 4055-4058. The Supporting Information for ref 9b states an erroneous CIP description - (1S,2R) - in the title for preparation of (+)-4 [(+)-4a, in our numbering], it should be (+)-(1R, 2S)-4.
    • (2000) Org. Lett. , vol.2 , pp. 4055-4058
    • Olivo, H.F.1    Velaquez, F.2    Trevisan, H.C.3
  • 12
    • 0035793253 scopus 로고    scopus 로고
    • The Olivo preparation (ref 9b) of (+)-4 from 1 was achieved using a four-step procedure which required two separate reduction steps in order to exploit an efficient lipase-catalyzed kinetic resolution of the primary alcohol. Paterson and co-workers prepared optically enriched 4 (98% ee) in two steps from epichlorohydrin (Paterson, I.; Davies, R. D. M.; Marquez, R. Angew. Chem., Int. Ed. 2001, 40, 603-607).
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 603-607
    • Paterson, I.1    Davies, R.D.M.2    Marquez, R.3
  • 13
    • 0035932078 scopus 로고    scopus 로고
    • The volatile aldehyde corresponding to 4 has also been prepared by Evans (five-step procedure from 1,2:5,6-di-O-cyclohexylidene-D-mannitol: Evans, D. A.; Burch, J. D. Org. Lett. 2001, 3, 503-505)
    • (2001) Org. Lett. , vol.3 , pp. 503-505
    • Evans, D.A.1    Burch, J.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.