메뉴 건너뛰기




Volumn 10, Issue 21, 2008, Pages 4787-4790

Synthesis of δ-tributylstannyl-α,βγ, δ-unsaturated aldehydes from pyridines

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BUTANE; PYRIDINE DERIVATIVE; TIN DERIVATIVE;

EID: 58149161579     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8020435     Document Type: Article
Times cited : (44)

References (60)
  • 3
    • 0027358491 scopus 로고    scopus 로고
    • Stannyldienals: (a) Yokokawa, F.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1993, 34, 6559-6562.
    • Stannyldienals: (a) Yokokawa, F.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1993, 34, 6559-6562.
  • 16
    • 0027050190 scopus 로고    scopus 로고
    • Stannyldienoic esters: (a) Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434-9453.
    • Stannyldienoic esters: (a) Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434-9453.
  • 29
    • 33645212849 scopus 로고    scopus 로고
    • Hosoya, T.; Sumi, K.; Doi, H.; Wakao, M.; Suzuki, M. Org. Biomol. Chem 2006, 4, 410-415. See also refs 3b, d.
    • (n) Hosoya, T.; Sumi, K.; Doi, H.; Wakao, M.; Suzuki, M. Org. Biomol. Chem 2006, 4, 410-415. See also refs 3b, d.
  • 34
    • 85069754511 scopus 로고
    • For reviews of Zincke chemistry, see: a
    • For reviews of Zincke chemistry, see: (a) Becher, J. Synthesis 1980, 589-611.
    • (1980) Synthesis , pp. 589-611
    • Becher, J.1
  • 36
    • 33745263963 scopus 로고    scopus 로고
    • Rojas, C. M. In Name Reactions in Heterocyclic Chemistry; Li, J. J., Ed.; John Wiley & Sons: Hoboken, NJ, 2005; pp 355-374.
    • (c) Rojas, C. M. In Name Reactions in Heterocyclic Chemistry; Li, J. J., Ed.; John Wiley & Sons: Hoboken, NJ, 2005; pp 355-374.
  • 39
    • 49349133364 scopus 로고    scopus 로고
    • The regioselectivity of addition of trimethylstannyllithium to enones has been studied: Still, W. C.; Mitra, A. Tetrahedron Lett. 1978, 19, 2659-2662.
    • The regioselectivity of addition of trimethylstannyllithium to enones has been studied: Still, W. C.; Mitra, A. Tetrahedron Lett. 1978, 19, 2659-2662.
  • 40
    • 37049091415 scopus 로고    scopus 로고
    • The conjugate addition of tin anions and stannylcopper reagents, in particular, is well documented. For examples, some of which include conjugate addition/elimination reactions to generate vinylstannanes from acceptors that bear excellent β-leaving groups, see: (a) Piers, E.; Morton, H. E. J. Chem. Soc., Chem. Commun. 1978, 1033-1034.
    • The conjugate addition of tin anions and stannylcopper reagents, in particular, is well documented. For examples, some of which include conjugate addition/elimination reactions to generate vinylstannanes from acceptors that bear excellent β-leaving groups, see: (a) Piers, E.; Morton, H. E. J. Chem. Soc., Chem. Commun. 1978, 1033-1034.
  • 45
    • 60949083812 scopus 로고    scopus 로고
    • 2SiLi with simple vinylogous amides. In one particular case, these authors found that the inclusion of an activated alkyl halide was required for successful outcomes, but this observation was not attributed to the reversibility of the process, nor was a satisfying explanation found. See: Fleming, I.; Marangon, E.; Roni, C.; Russell. M. G.; Taliansky Chamudis, S. Can. J. Chem. 2004, 82, 325-332.
    • 2SiLi with simple vinylogous amides. In one particular case, these authors found that the inclusion of an activated alkyl halide was required for successful outcomes, but this observation was not attributed to the reversibility of the process, nor was a satisfying explanation found. See: Fleming, I.; Marangon, E.; Roni, C.; Russell. M. G.; Taliansky Chamudis, S. Can. J. Chem. 2004, 82, 325-332.
  • 46
    • 0006625539 scopus 로고    scopus 로고
    • For the reversibility of trialkylstannyl anion additions to unsaturated electrophiles, see: Cox, S. D.; Wudl, F. Organometallics 1983, 2, 184-185. See also ref 8.
    • For the reversibility of trialkylstannyl anion additions to unsaturated electrophiles, see: Cox, S. D.; Wudl, F. Organometallics 1983, 2, 184-185. See also ref 8.
  • 47
    • 33750437727 scopus 로고    scopus 로고
    • ε-Vinylstannane 18 has only been made stereoselectively once, via a multistep sequence: Asano, M.; Inoue, M.; Watanabe, K.; Abe, H.; Katoh, T. J. Org. Chem. 2006, 71, 6942-6951.
    • ε-Vinylstannane 18 has only been made stereoselectively once, via a multistep sequence: Asano, M.; Inoue, M.; Watanabe, K.; Abe, H.; Katoh, T. J. Org. Chem. 2006, 71, 6942-6951.
  • 48
    • 0001739233 scopus 로고    scopus 로고
    • Stannane 20 is most frequently made by Lewis acid mediated acetylation of trans-1,2-bis(tributylstannyi)ethylene: (a) Peel, M. R.; Johnson, C. R. Tetrahedron Lett. 1986, 27, 5947-5950.
    • Stannane 20 is most frequently made by Lewis acid mediated acetylation of trans-1,2-bis(tributylstannyi)ethylene: (a) Peel, M. R.; Johnson, C. R. Tetrahedron Lett. 1986, 27, 5947-5950.
  • 49
    • 0011906205 scopus 로고    scopus 로고
    • It has been used in synthesis several times; for representative examples, see: (b) Johnson, C. R, Kadow, J. F. J. Org. Chem. 1987, 52, 1493-1500
    • It has been used in synthesis several times; for representative examples, see: (b) Johnson, C. R.; Kadow, J. F. J. Org. Chem. 1987, 52, 1493-1500.
  • 52
    • 33947480951 scopus 로고    scopus 로고
    • a of trialkylstannanes, see: (a) Gilman, H.; Marrs, O. L.; Trepka, W. J.; Diehl, J. W. J. Org. Chem. 1962, 27, 1260-1265.
    • a of trialkylstannanes, see: (a) Gilman, H.; Marrs, O. L.; Trepka, W. J.; Diehl, J. W. J. Org. Chem. 1962, 27, 1260-1265.
  • 54
    • 84982341931 scopus 로고    scopus 로고
    • Vinylogous amides from ketones and amide acetals: Meerwein, H.; Florian, W.; Schon, G.; Stopp, G. Liebigs Ann. Chem. 1961, 641, 1-39.
    • Vinylogous amides from ketones and amide acetals: Meerwein, H.; Florian, W.; Schon, G.; Stopp, G. Liebigs Ann. Chem. 1961, 641, 1-39.
  • 55
    • 60949097589 scopus 로고    scopus 로고
    • Tendency of ketone-derived vinylogous amides related to 23 to undergo conjugate addition/elimination with alkyllithium nucleophiles: Abdullah, R. F.; Fuhr, K. H. J. Org. Chem. 1978, 43, 4248-4250.
    • Tendency of ketone-derived vinylogous amides related to 23 to undergo conjugate addition/elimination with alkyllithium nucleophiles: Abdullah, R. F.; Fuhr, K. H. J. Org. Chem. 1978, 43, 4248-4250.
  • 56
    • 84922377851 scopus 로고    scopus 로고
    • Stannane 24 has been prepared by conjugate addition/elimination of the relevant β-iodoenone: Piers, E.; Morton, H. E.; Chong, J. M. Can. J. Chem. 1987, 65, 78-87.
    • Stannane 24 has been prepared by conjugate addition/elimination of the relevant β-iodoenone: Piers, E.; Morton, H. E.; Chong, J. M. Can. J. Chem. 1987, 65, 78-87.
  • 59
    • 60949095239 scopus 로고    scopus 로고
    • The conditions in Scheme 4 were derived from those detailed in ref 18b.
    • The conditions in Scheme 4 were derived from those detailed in ref 18b.
  • 60
    • 60949110094 scopus 로고    scopus 로고
    • While stannyldienals with substituents α to the aldehyde such as 10 and 14 (and presumably 16) generally cross-couple with retention of alkene geometries, stannane 12 readily isomerizes under Stille conditions, affording a mixture of product geometrical isomers. The inclusion of stoichiometric NEt3 suppressed isomerization in the synthesis of 26. A similar isomerization of the Z-isomer of 18 to the Ε-isomer under Stille conditions has been reported; see ref 18a
    • 3 suppressed isomerization in the synthesis of 26. A similar isomerization of the Z-isomer of 18 to the Ε-isomer under Stille conditions has been reported; see ref 18a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.