Categories: C-O Bond Formation
Synthesis of Hemiaminals and Hemiaminal ethers
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Recent Literature
An enantioselective addition of alcohols to imines proceeds in the presence of a
catalytic amount of a chiral phosphoric acid catalyst to give the respective
chiral N,O-aminals in excellent yield and enantioselectivity.
G. Li, F. R. Fronczek, J. C. Antilla, J. Am. Chem. Soc., 2008,
130, 12216-12217.
A cobalt-catalyzed decarboxylative acetoxylation reaction is applicable to a
wide range of amino acids and arylacetic acids.
K. Xu, Z. Wang, J. Zhang, L. Yu, J. Tan, Org. Lett.,
2015,
17, 4476-4478.
Unusual N-Acyl-N,O-acetals are present in a number of bioactive
natural products and can act as a synthetic precursor to unstable reactive
N-acylimines. Various N-acyl-N,O-acetals can be prepared
under mild conditions mediated by titanium ethoxide (Ti(OEt)4). The
method also offers a new strategy to make other O-alkyl-N,O-acetals.
M. Li, B. Luo, Q. Liu, Y. Hu, A. Ganesan, P. Huang, S. Wen, Org. Lett., 2014,
16, 10-13.
An I2-catalyzed oxidative cross-coupling of α-amino ketones with a
wide range of alcohols provides α-carbonyl N,O-acetals with high
functional group tolerance. Using a combination of air and dimethyl sulfoxide as
oxidants, the protocol allows an efficient late-stage modification of
biorelevant structures. Moreover, the use of other nucleophiles enables
additional functionalization of α-amino ketones.
Y. Wang, M. Yang, C. Lao, H. Wang, Z. Jiang, J. Org. Chem., 2023, 88,
14470-14486.
A highly efficient ruthenium-catalyzed stereospecific N-demethylative
rearrangement of isoxazolidines gives synthetically useful N-H-1,3-oxazinanes.
1,3-Oxazinanes are useful building blocks, which can be converted to
N-H-1,3-aminoalcohols in a subsequent step.
C.-Z. Yao, Z.-F. Xiao, X.-S. Ning, J. Liu, X.-W. Zhang, Y.-B. Kang, Org. Lett.,
2014,
16, 5824-5826.
ert-Butylperoxyamido acetals can be generated in high yields under
mild conditions via oxidative functionalization of C-H bonds adjacent to the amide nitrogen atom. Treatment with Grignard reagents enables the synthesis of
α-substituted amides.
H. Yu, J. Shen, Org. Lett., 2014,
16, 3204-3207.