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Volumn 125, Issue 39, 2003, Pages 12049-12056

Addition of organometallic compounds to tin-containing cyclic ketones. Remote stereocontrol induced by the stannyl group

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOMETALLIC REAGENTS;

EID: 0141843557     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036340c     Document Type: Article
Times cited : (12)

References (51)
  • 14
    • 0028906005 scopus 로고    scopus 로고
    • Nishigaichi, Y.; Kuramoto, M.; Takuwa, A. Tetrahedron Lett. 1995, 36, 3353; Chem. Lett. 1996, 961.
    • (1996) Chem. Lett. , pp. 961
  • 32
    • 0141523283 scopus 로고    scopus 로고
    • note
    • Acyclic ketones as 8 are of lesser utility, giving mixtures of diastereomeric alcohols (ca. 1:1) which are difficult to separate, whereas benzopiranone 12 leads to dirty mixtures of stannylated phenols resulting from lactone cleavage.
  • 33
    • 0141746402 scopus 로고    scopus 로고
    • note
    • We think that the high de observed in the RLi additions to 13 is not entirely due to the gem-dimethyl group but also due to the tin-effect. In fact, destannylation of 13 (HI/THF, room temperature) followed by Meli addition renders a lower stereoselectivity, now yielding mixtures of diastereomeric alcohols (ratio ca. 5.5:1), the major alcohol being the one with the expected syn (OH/gem-dimethyl) stereochemistry.
  • 34
    • 0003417469 scopus 로고
    • Trost, B., Fleming, I., Eds.; Pergamon, Elmsford, NY
    • It could be pointed out that torsional strain and steric factors developing in a transition state for 1,2-addition to ketones 9 and 10 would favor an equatorial (or pseudoequatorial) attack of the organolithium reagent leading to the observed stereochemistry; however, the extremely high diastereo-selectivity found with organolithium compounds is not consistent with literature data. In general, for substituted cyclopentanones, poor selectivities are reported (Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon, Elmsford, NY, 1991; Vol. 1), and even 3-tert-butylcyclohexanone, which probably is sterically more demanding than the 3-alkenyl-stannane derivative 10, reacts with MeLi giving only a 78:22(cis:trans) ratio (Rei, M. H. J. Org. Chem. 1979. 44, 2760).
    • (1991) Comprehensive Organic Synthesis , vol.1
  • 35
    • 0141634393 scopus 로고
    • It could be pointed out that torsional strain and steric factors developing in a transition state for 1,2-addition to ketones 9 and 10 would favor an equatorial (or pseudoequatorial) attack of the organolithium reagent leading to the observed stereochemistry; however, the extremely high diastereo-selectivity found with organolithium compounds is not consistent with literature data. In general, for substituted cyclopentanones, poor selectivities are reported (Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon, Elmsford, NY, 1991; Vol. 1), and even 3-tert-butylcyclohexanone, which probably is sterically more demanding than the 3-alkenyl-stannane derivative 10, reacts with MeLi giving only a 78:22(cis:trans) ratio (Rei, M. H. J. Org. Chem. 1979. 44, 2760).
    • (1979) J. Org. Chem. , vol.44 , pp. 2760
    • Rei, M.H.1
  • 36
    • 0141634396 scopus 로고    scopus 로고
    • note
    • Crystallographic data for the structure reported have been deposited in the Cambridge Crystallographic Data Centre, ref. no. CCDC-139911. Copies of the data can be obtained from the CCDC. 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
  • 39
    • 0141634394 scopus 로고    scopus 로고
    • note
    • w(C) = 1.7 Å.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.