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Volumn 74, Issue 12, 2009, Pages 4499-4507

A versatile route to (E)- and (Z)-2-hydroxy-3,4-unsaturated disubstituted sulfilimines and their haloamidation reaction

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; PROPARGYLIC ALCOHOLS; RU CATALYSTS; STEREOSELECTIVE PREPARATION;

EID: 67249157610     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900569z     Document Type: Article
Times cited : (12)

References (66)
  • 3
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    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • (a) Kemp, J. E. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol.3, pp 471-513.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 471-513
    • Kemp, J.E.G.1
  • 28
    • 67249089453 scopus 로고    scopus 로고
    • note
    • The cis-alkenes were obtained in nine steps from cis-2-butene-1,4-diol as depicted below. (Chemical Equation Presented)
  • 32
    • 0342621309 scopus 로고    scopus 로고
    • The β-hydroxy γ,δ-cis-alkenes cannot be derived from the reaction of cis esters with the lithio anion of aryl methyl sulfoxide followed by reduction of the resulting β-keto sulfoxides since the cis ester undergoes isomerization to the trans ester. The alternative reaction of acetylenic esters with lithio anion of aryl methyl sulfoxide followed by reduction of the resulting ynones suffers from poor stereoselectivity; see
    • The β-hydroxy γ,δ-cis-alkenes cannot be derived from the reaction of cis esters with the lithio anion of aryl methyl sulfoxide followed by reduction of the resulting β-keto sulfoxides since the cis ester undergoes isomerization to the trans ester. The alternative reaction of acetylenic esters with lithio anion of aryl methyl sulfoxide followed by reduction of the resulting ynones suffers from poor stereoselectivity; see: Sanchez-Obregon, R.; Ortiz, B.; Walls, F.; Yuste, F.; Garcia Ruano, J. L. Tetrahedron: Asymmetry 1999, 10, 947-955.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 947-955
    • Sanchez-Obregon, R.1    Ortiz, B.2    Walls, F.3    Yuste, F.4    Garcia Ruano, J.L.5
  • 34
    • 67249136004 scopus 로고    scopus 로고
    • note
    • p-Tolylthio acetaldehyde was obtained by IBX oxidation of p-tolylthio ethanol.
  • 35
    • 67249096044 scopus 로고    scopus 로고
    • note
    • In future, with an efficient catalyst becoming available for the preparation of propargylic alcohols, by the direct reaction of aldehydes and alkynes, we can prepare optically active sulfilimines with excellent enantioselectivity readily in only three steps.
  • 36
    • 0029836898 scopus 로고    scopus 로고
    • For other alternative approaches to the reduction of ynones, see
    • For other alternative approaches to the reduction of ynones, see: (a) Helal, C. J.; Magriotis, P. A.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 10938-11939
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 10938-11939
    • Helal, C.J.1    Magriotis, P.A.2    Corey, E.J.3
  • 47
    • 67249161000 scopus 로고    scopus 로고
    • note
    • The enantioselectivity was determined by chiral HPLC; see the Supporting Information. The S configuration was assigned on the basis of literature precedent.
  • 48
    • 67249113344 scopus 로고    scopus 로고
    • note
    • The hydrogenation in EtOAc as the solvent afforded the alcohol in poor yield. The substrate to catalyst ratio (25:1) was found to be optimal. With a higher substrate to catalyst ratio (100:1) side reactions were observed.
  • 58
    • 67249154290 scopus 로고    scopus 로고
    • note
    • 1H NMR to the corresponding N-Ts-sulfilimines.
  • 59
    • 61349127170 scopus 로고    scopus 로고
    • and references cited therein
    • Collet, F.; Dodd, R. H.; Dauban, P. Org. Lett. 2008, 10, 5473-5476, and references cited therein.
    • (2008) Org. Lett. , vol.10 , pp. 5473-5476
    • Collet, F.1    Dodd, R.H.2    Dauban, P.3
  • 60
    • 33748542524 scopus 로고
    • For reviews of the effects of 1,3-allylic strain on conformation and stereoselectivity, see
    • For reviews of the effects of 1,3-allylic strain on conformation and stereoselectivity, see: (a) Johnson, F. Chem. Rev. 1968, 68, 375-413.
    • (1968) Chem. Rev. , vol.68 , pp. 375-413
    • Johnson, F.1
  • 66
    • 67249092759 scopus 로고    scopus 로고
    • See the Supporting Information
    • See the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.