Categories: C=C Bond Formation >
Synthesis of 1,3-dienes
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Recent Literature
Lithiated allylic phosphonates undergo efficient olefination reactions with a
variety of aldehydes in the presence of HMPA to give terminal 1,3-dienes with
high selectivity for the E-isomer. This method is general and
procedurally simple.
Y. Wang, F. G. West, Synthesis, 2002, 99-103.
Cross metathesis of terminal alkenes with methyl (2Z,4E)-hexadienoate
and related dienyl esters promoted by the standard second-generation
Grubbs-Hoveyda catalyst provides substituted (2Z,4E)-dienyl esters
in good yields. A fluorous catalyst is used for separation and recovery in
gram-scale reactions.
G. Moura-Letts, D. P. Curran, Org. Lett., 2007,
9, 5-8.
A versatile and operationally simple base-catalyzed multi-component domino
reaction between α,β-unsaturated carbonyl compounds, aldehydes, and alcohols is
described, providing a new efficient, and stereoselective one-pot preparation of
trisubstituted alkenes and 1,3-dienes.
H. Habib-Zahmani, S. Hacini, C. Bories, J. Rodriguez, Synthesis, 2005,
2151-2156.
A gold(I)-catalyzed rearrangement of diversely substituted allenyl carbinol
esters allows the efficient, rapid, and stereoselective synthesis of various
functionalized 1,3-butadien-2-ol esters via a new 1,3-shift of an ester moiety
onto a gold-activated allene.
A. K. Buzas, F. M. Istrate, F. Gagosz, Org. Lett., 2007,
9, 985-988.
Deprotonation of 3,3,3-trichloropropyl-1-triphenylphosphonium chloride
generates the corresponding phosphorane, which reacts with aldehydes to give
trichloromethylated (Z)-olefins, which are useful for the synthesis
of (Z)-1,3-enynes, (Z,Z)-1-chloro-1,3-dienes, and 1,3-diynes
in high yields and stereospecificities.
M. S. Karatholuvhu, P. L. Fuchs, J. Am. Chem. Soc.,
2004, 126, 14314-14315.
Heating with NaI and DBU in dimethoxyethane effected clean
elimination of tosylates to terminal olefins. This simple one-pot procedure was
also applied to tosylates derived from an Evans Aldol Reaction.
P. Phukan, M. Bauer, M. E. Maier, Synthesis, 2003, 1324-1328.
Ruthenium-Catalyzed Tandem Cross-Metathesis/Wittig Olefination: Generation
of Conjugated Dienoic Esters from Terminal Olefins
R. P. Murelli, M. L. Snapper, Org. Lett., 2007,
9, 1749-1752.
The GaCl3-catalyzed skeletal
reorganization of enynes is
simple and provides a diverse range of dienes in good to high yields. The
reaction of enynes
proceeds in a stereospecific manner with respect to the geometry of the olefin
moiety.
N. Chatani, H. Inoue, T. Kotsuma, S. Murai, J. Am. Chem. Soc., 2002, 124, 10294-10295.
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