Categories: C=C Bond Formation >
Synthesis of 1,3-dienes
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Name Reactions
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.
N-sulfonyl imines undergo olefination reactions with various
benzylidenetriphenylphosphoranes or allylidenetriphenylphosphoranes under mild
reaction conditions to afford an array of both Z- and E-isomers of
conjugated alkenes in good to excellent yields and with greater than 99:1
stereoselectivity depending on the N-sulfonyl group.
D.-J. Dong, H.-H. Li, S.-K. Tian, J. Am. Chem. Soc., 2010,
132, 5018-5020.
Synthesis of 1,3-diene from alkyne and ethylene (1 atm) was improved using a
ruthenium NHC carbene complex having a heterocyclic carbene as a ligand. Various
1,3-dienes could be synthesized from alkynes and ethylene.
K. Tonogakia, M. Mori, Tetrahedron Lett.,
2002,
43, 2235-2238.
A stereoselective synthesis of dienes from aldehydes and N-allylhydrazine
derivatives offers high levels of (E)-stereoselectivity for a variety of
substrates. Addition of a dienophile to the reaction mixture allows a one-flask
diene synthesis-cycloaddition sequence.
D. A. Mundal, K. E. Lutz, R. J. Thomson, Org. Lett., 2009,
11, 465-468.
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.
Wittig Olefination between Phosphine, Aldehyde, and Allylic Carbonate: A
General Method for Stereoselective Synthesis of Trisubstituted 1,3-Dienes with
Highly Variable Substituents
R. Zhou, C. Wang, H. Song, Z. He, Org. Lett., 2010,
12, 976-979.
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 highly stereoselective Rh(I)-catalyzed 1,3-acetoxyl rearrangement of
1,2-allen-3-yl carboxylates leads to 2-acetoxy-1,3(E)-alkadienes.
Features of the reaction are a high catalytic efficiency, broad scope and
excellent E-selectivity.
X. Zhang, C. Fu, S. Ma, Org. Lett., 2011,
13, 1920-1923.
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.
Highly regio- and stereoselective reactions of readily available
2-(methoxycarbonyl)-2,3-allenols with oxalyl chloride in the presence of Et3N
or DMSO afforded methyl 2-(ethynyl)alk-2(E)-enoates and
2-(1′-chlorovinyl)alk-2(Z)-enoates, respectively, in good yields.
Y. Deng, X. Kin, C. Fu, S. Ma, Org. Lett., 2009,
11, 2169-2172.
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.
Pd(0)-catalyzed carbonylation of (Z)-2-en-4-yn carbonates in the presence
of CO and an alcohol gives vinylallenyl esters with an exclusively E-configuration
in high yields. The unreactivity of E-configured enyne carbonates may
indicate that the reaction is promoted via the cooperative coordination of
palladium with both alkynyl and carbonate moieties.
G. E. Akpınar, M. Kuş, M. Uçncu, E. Karakuş, L. Artok, Org. Lett., 2011,
13, 748-751.
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