Palladium-catalyzed intra-molecular olefin insertion reaction of α-alkenyl-α-acyloxytrialkylsilane. Synthesis of optically active carbocycle

Tetrahedron Letters

Volumn 48, Issue 22, 2007, Pages 3925-3928

  Sakaguchi, Kazuhiko ^a   Okada, Takuya ^a   Yamada, Takeshi ^a   Ohfune, Yasufumi ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

Acyloxysilane; Allyl palladium; Chirality transfer; Olefin insertion; Pd catalyzed cyclization; Vinylsilane

Indexed keywords

ALKENE; ALPHA ALKENYL ALPHA ACYLOXYTRIALKYLSILANE DERIVATIVE; CARBON MONOXIDE; PALLADIUM; SILANE DERIVATIVE; UNCLASSIFIED DRUG; VINYLSILANE;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 34247633037     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.029     Document Type: Article

References (27)

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15. 3) δ 5.82 (dd, J = 18.4, 7.1 Hz, 1H), 5.68 (d, J = 18.4 Hz, 1H), 4.98 (d, J = 2.0 Hz, 1H), 4.79 (d, J = 2.0 Hz, 1H), 3.74 (s, 3H), 3.72 (s, 3H), 3.17 (m, 1H), 3.07 (m, 1H), 2.94 (m, 1H), 2.58 (dd, J = 13.0, 7.7 Hz, 1H), 2.03 (dd, J = 13.0, 11.0 Hz, 1H), 0.86 (s, 9H), 0.01 (s, 6H).
16. 3) δ 6.00 (dd, J = 18.7, 7.0 Hz, 1H), 5.70 (dd, J = 18.7, 0.9 Hz, 1H), 4.75 (d, J = 1.5, 1H), 4.61 (d, J = 1.5 Hz, 1H), 3.78 (s, 3H), 3.70 (s, 3H), 2.84 (m, 1H), 2.47-2.32 (4H), 1.83-1.66 (2H), 0.87 (s, 9H), 0.02 (s, 6H).
17. 1H NMR showed signals corresponding to a trans-vinylsilane (5.6-6.0 ppm, J = 18.4-18.7 Hz) and an internal olefin.{A figure is presented}
18. The yield of a Pd-catalyzed six-membered ring formation was also moderate (63%), see Ref. 7.
19. 1H NMR using the mixture of the corresponding MTPA esters (Supplementary data). Although the absolute configuration of 3 was not confirmed, it was suggested to be R by consideration of the result of 2.
20. 3, and DPPE) did not improve the yield of 3.
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26. 3) δ 7.04 (dd, J = 9.9, 0.5 Hz, 1H), 6.00 (dd, J = 9.9, 2.6 Hz, 1H), 3.75 (s, 3H), 3.74 (s, 3H), 2.79 (dd, J = 12.8, 6.9 Hz, 1H), 2.74 (dd, J = 16.5, 3.6 Hz, 1H), 2.66 (dd, J = 12.8, 6.0 Hz, 1H), 2.41 (m, 1H), 2.20 (dd, J = 16.5, 13.7 Hz, 1H), 2.04 (m, 1H), 1.90 (dd J = 12.8, 6.6 Hz, 1H), 1.88 (dd, J = 12.8, 6.2 Hz, 1H).
27. The J values of the ring-junction protons of both cis-8 and trans-8 were obtained by the homonuclear decoupling method.