Categories: Synthesis of N-Heterocycles >
Synthesis of 1,2,3,6-tetrahydropyridines
Recent Literature
A palladium-catalyzed highly 6-endo-selective alkyl-Heck reaction of
unactivated alkyl iodides provides efficient access to various
5-phenyl-1,2,3,6-tetrahydropyridine derivatives, which are important structural
motifs for bioactive molecules. Mechanistic investigations reveal a hybrid
palladium-radical process.
X. Dong, Y. Han, F. Yan, Q. Liu, P. Wang, K. Chen, Y. Li, Z. Zhao, Y. Dong, H.
Liu, Org. Lett.,
2016, 18, 3758-3761.
Acid-promoted condensations of N-[(Z)-3-iodoallyl]-aminoacetaldehydes
and hydrazine hydrate followed by Pd-catalyzed asymmetric intramolecular
hydrazone-type Heck reactions provide allylic diazenes that rapidly undergo
stereospecific denitrogenative [1,5]-sigmatropic rearrangement, furnishing
3-substituted tetrahydropyridines with high enantioselectivity.
S. Yu, L. Zhou, S. Ye, X. Tong, J. Am. Chem. Soc.,
2023, 145, 7621-7627.
The ion-paired Lewis acid [FeCl2]+[FeCl4]-
generated by the in situ disproportionation of FeCl3 catalyzes an
aza-Diels-Alder reaction of nonactivated dienes and imines.
R. Tomifuji, J. Maeda, T. Takahashi, T. Kurahashi, S. Matsubara, Org. Lett.,
2018, 20, 7474-7477.
An efficient palladium-catalyzed Heck/Suzuki tandem reaction of (Z)-1-iodo-1,6-dienes
with organoboronic acids provides various tetrahydropyridines in good to
excellent yields under mild reaction conditions. An asymmetric version of this
reaction is investigated to deliver chiral tetrahydropyridine in excellent yield
with promising enantioselectivity.
S. Yu, Z. Jin, X. Tong, L. Qi, Org. Lett., 2024,
26, 2175-2179.
[Et3NH]+[BF4]- as an H-bond donor in a toluene/water/(CH2OH)2 biphasic system efficiently
promotes a transition-metal catalyzed carbon-halogen reductive elimination at low temperature. This enables a
series of Pd(0)-catalyzed carbohalogenation reactions, including an unprecedented asymmetric carbobromination
in the presence of readily available ligands.
X. Chen, J. Zhao, M. Dong, N. Yang, J. Wang, Y. Zhang, K. Liu, X. Tong, J. Am. Chem. Soc.,
2021, 143, 1924-1931.