Categories: C-N Bond Formation > Amines > Amino Alcohols
Synthesis of β-amino alcohols
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Recent Literature
Zinc(II) perchlorate hexahydrate is a highly efficient catalyst for the opening
of epoxides by amines affording 2-amino alcohols in high yields under
solvent-free conditions and with excellent chemo-, regio-, and
stereoselectivities.
Shivani, B. Pujala, A. K. Chakraborti, J. Org. Chem., 2007,
72, 3713-3722.
The mild aminolysis of a variety of epoxides in water gave β-amino alcohols with high selectivity and in excellent yields
in the absence of any catalyst.
N. Azizi, M. R. Saidi, Org. Lett., 2005,
7, 3649-3651.
Highly regioselective ring opening of epoxides with poor nucleophiles such as
indole, borane, O-trimethylsilylhydroxylamine, p-nitroaniline and
sterically hindered tert-butylamine is a fast and convenient reaction in
the presence of 5.0 M lithium perchlorate-Et2O solution (LPDE).
A. Heydari, M. Mehrdad, A. Maleki, N. Ahmadi, Synthesis, 2004,
1557-1558.
Sc(OSO3C12H25)3 catalyses the
asymmetric ring opening of meso-epoxides with aromatic amines in the presence of
1.2 mol-% of a chiral bipyridine ligand to afford β-amino alcohols in
high yields with excellent enantioselectivities using water as environmentally
benign solvent.
S. Azoulay, K. Manabe, S. Kobayashi, Org. Lett.,
2005,
7, 4593-4595.
A mild, calcium trifluoromethanesulfonate-catalyzed aminolysis of epoxides is
very efficient in the synthesis of various β-amino alcohols with high regio-
and stereoselectivity.
I. Cepanec, M. Litvic, H. Mikuldas, A. Bartolincic,
V. Vinkovic, Tetrahedron, 2003, 59, 2435-2439.
Silica gel (60–120 mesh)
efficiently catalyses the opening of epoxides by amines at r.t. under
solvent-free conditions. Non-styrenoidal unsymmetrical alkene oxides undergo
selective nucleophilic attack at the sterically less hindered carbon by
aniline. A complementary regioselectivity is exhibited by aromatic and
aliphatic amines during the reaction with styrene oxide.
A. K. Chakraborti, S. Rudrawar, A. Kondaskar, Org.
Biomol. Chem., 2004, 2, 1277-1280.
An efficient, directed reductive amination of β-hydroxy-ketones allows the
stereoselective preparation of 1,3-syn-amino alcohols using Ti(iOPr)4
for coordination of the intermediate imino alcohol and PMHS as the reducing
agent.
D. Menche, F. Arikan, J. Li, S. Rudolph, Org. Lett., 2007,
9, 267-270.
Biologically important N-β-hydroxyethylaziridine intermediates were
conveniently prepared by regioselective ring-opening reactions of various
epoxides with in situ-generated ethyleneimine
from β-chloroethylamine under basic conditions in an aqueous environment.
H. Y. Kim, A. Talukdar, M. Cushman, Org. Lett.,
2006,
8, 1085-1087.
A simple, efficient, and environmentally benign methodology allows the synthesis
of β-amino alcohols from aromatic amines and alkylene carbonates in the presence
of the highly active and reusable solid base catalyst Na-Y zeolite.
A. B. Shivarkar, S. P. Gupte, R. V. Chaudhari, Synlett,
2006, 1374-1378.
An intermolecular Pd-catalyzed aminoacetoxylation of alkenes with phthalimide
as the nitrogen source and PhI(OAc)2 as the stoichiometric oxidant
and source of acetate achieves a highly regio- and diastereoselective oxidative
1,2-difunctionalization of alkenes. The mechanism is discussed.
G. Liu, S. S. Stahl, J. Am. Chem. Soc.,
2006,
128, 7179-7181.
