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Volumn , Issue 2, 2005, Pages 289-293

Unexpected cis-selectivity in (Sylvestre) Julia Olefinations with Bu 3Sn-containing allyl benzothiazolyl sulfones: Stereoselective synthesis of 1,3-butadienyl- and 1,3,5-hexatrienylstannanes

Author keywords

Alkenylstannanes; Dienes; Julia Lythgoe olefination; Stereoselectivity; Trienes

Indexed keywords

1,3 BUTADIENYLSTANNANE DERIVATIVE; 1,3,5 HEXATRIENYLSTANNANE DERIVATIVE; ALDEHYDE; ALLYL BENZOTHIAZOLYL SULFONE DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; BENZOTHIAZOLYLSULFONE DERIVATIVE; SULFONE DERIVATIVE; TIN DERIVATIVE; TRIBUTYLTIN; UNCLASSIFIED DRUG;

EID: 13844262686     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-837213     Document Type: Article
Times cited : (39)

References (43)
  • 12
    • 0029933368 scopus 로고    scopus 로고
    • (D) For an exception see: Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285 : A 71:29 cis:trans ratio was observed for the hexatrienes resulting from an a-lithioallyl benzothiazolyl sulfone and an a,b-unsaturated aldehyde. This ratio was increased to 82:18 employing the a-potassioallyl benzothiazolyl sulfone.
    • (1996) Synthesis , pp. 285
    • Bellingham, R.1    Jarowicki, K.2    Kocienski, P.3    Martin, V.4
  • 13
    • 8644283571 scopus 로고    scopus 로고
    • (e) Note added in proof: A 75:25 cis:trans ratio has been published recently for the (Sylvestre) Julia olefmation of a multiply conjugated aldehyde with an α-sodiopentadienyl benzothiazolyl sulfone: Furuichi, N.; Hara, H.; Osaki, T.; Nakano, M.; Mori, H.; Katsumura, S. J. Org. Chem. 2004, 69, 7949.
    • (2004) J. Org. Chem. , vol.69 , pp. 7949
    • Furuichi, N.1    Hara, H.2    Osaki, T.3    Nakano, M.4    Mori, H.5    Katsumura, S.6
  • 21
    • 13844289551 scopus 로고
    • Universität Würzburg
    • (a) Lankat, R. Diplomarbeit; Universität Würzburg, 1992, 25.
    • (1992) Diplomarbeit , pp. 25
    • Lankat, R.1
  • 22
    • 13844289551 scopus 로고
    • Universität Würzburg
    • (b) Lankat, R. Diplomarbeit; Universität Würzburg, 1992, 28.
    • (1992) Diplomarbeit , pp. 28
    • Lankat, R.1
  • 26
    • 13844273551 scopus 로고    scopus 로고
    • note
    • 2 (m/z = 681.26548).
  • 27
    • 13844284529 scopus 로고    scopus 로고
    • Dissertation; Universität Freiburg
    • Sorg, A. Dissertation; Universität Freiburg, 2004.
    • (2004)
    • Sorg, A.1
  • 28
    • 13844273552 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra and provided correct combustion analyses or high resolution mass spectra.
  • 30
    • 13844284528 scopus 로고    scopus 로고
    • note
    • 24 catalysis: see ref.3b
  • 32
    • 13844286318 scopus 로고    scopus 로고
    • note
    • Cis:trans ratios up to >99:1 for (Sylvestre) Julia olefmations of pentanal or octanal with (γ-butylpropargyl) benzothiazolyl sulfone, LiBr, and LDA in THF: see ref.3c
  • 34
    • 13844259633 scopus 로고    scopus 로고
    • following paper
    • After terminating the present study, we learned that Professor de Lera and associates observed cis-selective (Sylvestre) Julia olefinations, too, starting from a series of polyenyl benzothiazolyl sulfones including sulfone 1f. In their study, these authors (Vaz, B.; Alvarez, R.; Souto, J. A.; de Lera, A. R. Synlett 2005, following paper) had independently revised the stereochemical outcome of their olefination 1f + 2 → 3 in favor of the selectivity depicted in Scheme 1.
    • (2005) Synlett
    • Vaz, B.1    Alvarez, R.2    Souto, J.A.3    De Lera, A.R.4
  • 37
    • 33748215548 scopus 로고
    • Kiehl, A.; Eberhardt, A.; Adam, M.; Enkelmann, V.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1992, 31, 1588; Angew. Chetn. 1992, 104, 1623.
    • (1992) Angew. Chetn. , vol.104 , pp. 1623


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.