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Volumn 130, Issue 49, 2008, Pages 16500-16501

Convergent and stereoselective synthesis of trisubstituted E-alkenyl bromides and iodides via β-oxido phosphonium ylides

Author keywords

[No Author keywords available]

Indexed keywords

6 BROMOHEXADECA 5,9 DIENOIC ACID; ALKENYL GROUP; BROMIDE; FATTY ACID; IODIDE; PHOSPHONIUM DERIVATIVE; PHOSPHORANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 57549083600     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8076999     Document Type: Article
Times cited : (29)

References (34)
  • 1
  • 11
    • 0001071115 scopus 로고
    • Schreiber, S. L, Ed, Pergamon Press: Oxford
    • Kelly, S. E. In Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, pp 729-817.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 729-817
    • Kelly, S.E.1
  • 12
    • 57549098114 scopus 로고    scopus 로고
    • 2nd ed, Schlosser, M, Ed, Wiley: Chichester
    • (a) Organometallics in Synthesis: A Manual, 2nd ed.; Schlosser, M., Ed.; Wiley: Chichester, 2003.
    • (2003) Organometallics in Synthesis: A Manual
  • 14
    • 57549097686 scopus 로고    scopus 로고
    • Mulzer, J, Ed, Thieme: Stuttgart
    • (c) Pollex, A. In Science of Synthesis; Mulzer, J., Ed.; Thieme: Stuttgart, 2008; Vol. 32, pp 431-532.
    • (2008) Science of Synthesis , vol.32 , pp. 431-532
    • Pollex, A.1
  • 15
    • 0000064657 scopus 로고    scopus 로고
    • All yields reported are for chromatographically purified products. All E/Z ratios reported were determined on crude reaction mixtures by GC/MS; in some cases, slight variation was observed following chromatographic purification (ref 10). E/Z assignments were based on NOE studies; also usefully diagnostic is the fact that =CH cis to Br (or I) is uniformly at larger chemical shift relative to =CH trans to Br (or I). For an unambiguous example supporting this, see: Brown, H. C.; Bhat, N. G.; Rajagopalan, S. Synthesis 1986, 480-482.
    • All yields reported are for chromatographically purified products. All E/Z ratios reported were determined on crude reaction mixtures by GC/MS; in some cases, slight variation was observed following chromatographic purification (ref 10). E/Z assignments were based on NOE studies; also usefully diagnostic is the fact that =CH cis to Br (or I) is uniformly at larger chemical shift relative to =CH trans to Br (or I). For an unambiguous example supporting this, see: Brown, H. C.; Bhat, N. G.; Rajagopalan, S. Synthesis 1986, 480-482.
  • 16
    • 57549103826 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 17
    • 57549110877 scopus 로고    scopus 로고
    • 3OPh, 59%).
    • 3OPh, 59%).
  • 18
    • 0001366507 scopus 로고
    • 3P=CRBr (or I)] are known to be nonstereoselective (unless R = Me, which leads to Z-selectivity); see: (a) Smithers, R. H
    • 3P=CRBr (or I)] are known to be nonstereoselective (unless R = Me, which leads to Z-selectivity); see: (a) Smithers, R. H. J. Org. Chem. 1978, 43, 2833-2838.
    • (1978) J. Org. Chem , vol.43 , pp. 2833-2838
  • 20
    • 57549099488 scopus 로고    scopus 로고
    • For routes to E-alkenyl bromides via hydroboration of 1-bromo-1-alkynes using organoboranes, see: (a) ref 9.
    • For routes to E-alkenyl bromides via hydroboration of 1-bromo-1-alkynes using organoboranes, see: (a) ref 9.
  • 23
    • 0043087111 scopus 로고    scopus 로고
    • For chloroalkene synthesis from a β-oxido ylide where the alkene stereochemistry depends on the source of electrophilic chlorine, see: Corey, E. J, Shulman, J. I, Yamamoto, H. Tetrahedron Lett. 1970, 11, 447-450
    • For chloroalkene synthesis from a β-oxido ylide where the alkene stereochemistry depends on the source of electrophilic chlorine, see: Corey, E. J.; Shulman, J. I.; Yamamoto, H. Tetrahedron Lett. 1970, 11, 447-450.
  • 29
    • 84981574760 scopus 로고    scopus 로고
    • In the present case, phosphonium salt 10 was prepared in 3 steps from ethyne via hexylcupration-alkylation (Alexakis, A, Cahiez, G, Normant, J. F. Synthesis 1979, 826-830) with 3-chloro-1- iodopropane see Supporting Information
    • In the present case, phosphonium salt 10 was prepared in 3 steps from ethyne via hexylcupration-alkylation (Alexakis, A.; Cahiez, G.; Normant, J. F. Synthesis 1979, 826-830) with 3-chloro-1- iodopropane (see Supporting Information).
  • 31
    • 57549115459 scopus 로고    scopus 로고
    • 2Br gave alkenyl bromide 12 in 76% yield.
    • 2Br gave alkenyl bromide 12 in 76% yield.
  • 34
    • 1642431261 scopus 로고    scopus 로고
    • For a discussion, and alternative solution to E-alkenyl iodides, see: Zou, M.-F.; Deng, M.-Z. J. Org. Chem. 1996, 61, 1857-1858.
    • For a discussion, and alternative solution to E-alkenyl iodides, see: Zou, M.-F.; Deng, M.-Z. J. Org. Chem. 1996, 61, 1857-1858.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.