TY - JOUR
T1 - Palladium(0)-catalyzed cis-selective alkylative and arylative cyclization of alkynyl enones with organoboron reagents
AU - Tsukamoto, Hirokazu
AU - Suzuki, Takamichi
AU - Uchiyama, Tomomi
AU - Kondo, Yoshinori
N1 - Funding Information:
This work was partly supported by a Grant-in-Aid from the Japan Society for Promotion of Sciences (No.18790003) and Banyu Pharmaceutical Co. Ltd Award in Synthetic Organic Chemistry, Japan.
PY - 2008/6/23
Y1 - 2008/6/23
N2 - A palladium(0)-tricyclohexylphosphine catalyzes cis-selective alkylative and arylative cyclization of alkyne-containing electron-deficient alkenes with organoboron reagents to provide five- or six-membered rings with exo tri- or tetra-substituted alkenes. The opposite stereoselectivity to that for the alkyne-aldehyde cyclization using the same reagents would result from palladacycle-forming oxidative addition of the substrates to the Pd0 catalyst followed by transmetalation with the boron reagents, protonation, and reductive elimination. The functional group compatibility, availability, stability, and non-toxicity of the reagents, and the fact that no additives are needed make the process more practical than the Ni0-catalyzed cyclization with organozinc reagents.
AB - A palladium(0)-tricyclohexylphosphine catalyzes cis-selective alkylative and arylative cyclization of alkyne-containing electron-deficient alkenes with organoboron reagents to provide five- or six-membered rings with exo tri- or tetra-substituted alkenes. The opposite stereoselectivity to that for the alkyne-aldehyde cyclization using the same reagents would result from palladacycle-forming oxidative addition of the substrates to the Pd0 catalyst followed by transmetalation with the boron reagents, protonation, and reductive elimination. The functional group compatibility, availability, stability, and non-toxicity of the reagents, and the fact that no additives are needed make the process more practical than the Ni0-catalyzed cyclization with organozinc reagents.
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U2 - 10.1016/j.tetlet.2008.04.111
DO - 10.1016/j.tetlet.2008.04.111
M3 - Article
AN - SCOPUS:43849100005
SN - 0040-4039
VL - 49
SP - 4174
EP - 4177
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 26
ER -