Categories: Synthesis of N-Heterocycles, Synthesis of O-Heterocycles >
Synthesis of oxazolidines
Recent Literature
A highly efficient one-pot synthesis of a wide range of 1,3-oxazolidines and
1,3-oxazinanes in high yields and with excellent enantioselectivities proceeds
in the presence of a chiral magnesium phosphate catalyst via the formation of
hemiaminal intermediates obtained by the enantioselective addition of respective
alcohols to imines followed by intramolecular cyclization under mildly basic
conditions.
S. K. Nimmagadda, Z. Zhang, J. C. Antilla, Org. Lett.,
2014,
16, 4098-4101.
The reaction of aliphatic aldehydes with nonstabilized azomethine ylides
provides oxazolidines, pyrrolidines, or Mannich bases, depending on the
structure of the starting compound and the reaction conditions.
E. V. Gorbunova, E. M. Buev, V. S. Moshkin, V. Y. Sosnovskikh, Synlett, 2020,
31,
343-348.
Tetrabutylammonium iodide as the catalyst and tert-butyl hydroperoxide
in water (T-Hydro) as the oxidant enable a potential route for the construction
of functionalized oxazolidines and imidazolidines via oxidative C(sp3)-H
functionalization/C-O/C-N
bonds formations. The reaction is simple, regioselective, and effective at
moderate temperature with broad substrate scope.
V. Satheesh, M. Sengoden, T. Punniyamurthy, J. Org. Chem.,
2016, 81, 9792-9801.
An operationally simple and efficient AgOTf-promoted tandem olefin
isomerization/intramolecular hydroamination of 1,1-disubstituted alkenyl amines
provides diverse 2-alkyl-substituted 1,3-X,N-heterocycles in very good yields
through chemo- and regioselective C(sp3)-N bond formation with high
atom economy. The reaction offers high functional group tolerance and broad
substrate scope.
Y. H. Kim, D. B. Kim, S. W. Youn, J. Org. Chem., 2022, 87,
11919-11924.
An efficient iron porphyrin Lewis acid-catalyzed cycloaddition of aziridines
with aldehydes provide oxazolidines with high regio- and diastereoselectivity.
The cycloaddition proceeds in toluene with 1 mol % of the iron catalyst at 25°C.
S. Teranishi, K. Maeda, T. Kurahashi, S. Matsubara,
Org. Lett., 2019, 21, 2593-2596.
Bisphosphine-catalyzed mixed double-Michael reactions between amino-acid-derived
pronucleophiles as Michael donors and electron-deficient acetylenes as acceptors
afford β-amino carbonyl derivatives of oxazolidines, thiozolidines, and
pyrrolidines in excellent yields and with high diastereoselectivities under
operationally simple and mild conditions.
V. Sriramurthy, G. A. Barcan, O. Kwon, J. Am. Chem. Soc., 2007,
129, 12928-12929.
A stereoselective synthesis of 2,4- and 2,5-disubstituted 1,3-oxazolidines is
accomplished via Pd-catalyzed carboamination of O-vinyl-1,2-amino alcohol
derivatives. The transformations generate cis-disubstituted products with
good to excellent diastereoselectivity, and enantiomerically enriched substrates
are converted without loss of optical purity.
A. F. Ward, J. P. Wolfe, Org. Lett., 2011,
13, 4728-4731.
A palladium complex generated in situ from [Pd2(dba)3]·CHCl3
and a phosphoramidite ligand catalyzes an efficient enantioselective synthesis
of 4-substituted-4-vinyloxazolidines through decarboxylative cycloaddition of
vinylethylene carbonates with imines under mild reaction conditions in very good
yields with high levels of enantio- and diastereoselectivities.
L. Yang, A. Khan, R. Zhen, L. Y. Jin, Y. J. Zhang, Org. Lett.,
2015,
17, 6230-6233.