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.
A variety of polar mixed solvent systems enable an efficient and regioselective
synthesis of β-amino alcohols from a variety of epoxides and primary amines in
high yields in the absence of any catalyst.
J. R. Lizza, G. Moura-Letts, Synthesis, 2017,
49, 1231-1242.
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 readily synthesized chiral sulfinamide based organocatalyst enables an
asymmetric ring-opening (ARO) reaction of meso epoxides with anilines in
high yields of with excellent enantioselectivity at room temperature. A probable
mechanism for the catalytic ARO reaction is envisaged by 1H and
13C NMR experiments.
M. Kumar, R. I. Kureshy, S. Saravanan, S. Verma, A. Jakhar, N.-u. H. Khan, S. H.
R. Abdi, H. C. Bajaj, Org. Lett., 2014,
16, 2798-2801.
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.
In a radical-mediated strategy for β C-H amination of alcohols, imidates as
radical relay chaperones serve as traceless directors that facilitates selective
C-H functionalization via 1,5-hydrogen atom transfer (HAT) and enable net
incorporation of ammonia at the β carbon. A streamlined protocol enables rapid
conversion of alcohols to their β-amino analogs (via in situ conversion of
alcohols to imidates, directed C-H amination, and hydrolysis).
E. A. Wappes, K. M. Nakafuku, D. A. Nagib, J. Am. Chem. Soc., 2017,
139, 10204-10207.
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 yttrium-catalyzed regioselective ring-opening reaction of 2,3-epoxy esters
and amides with amines as nucleophiles features high regiocontrol, an
enantiospecific SN2 reaction pathway, a broad substrate scope, and
mild reaction conditions. The reaction furnishes a wide range of α-hydroxy
β-amino esters and amides in regioisomerically pure forms.
H. Yao, C. Wang, Synlett, 2023,
34,
2471-2475.
Photoredox-catalyzed and nitrogen-centered radical-triggered cascade reactions
of styrenes (or phenylacetylenes), enol derivatives, and O-acyl
hydroxylamines in DMSO provide functionalized β-amino alcohols. Structurally
diverse reaction components, including complex molecular scaffolds can be
converted.
X.-D. An, Y.-Y. Jiao, H. Zhang, Y. Gao, S. Yu, Org. Lett.,
2018, 20, 401-404.
A catalytic, highly C3-selective, stereosepecific ring-opening reaction of
2,3-epoxy alcohols and 2,3-epoxy sulfonamides is efficiently promoted by W-salts.
The developed method was applicable to various epoxides with diverse N-
and O-nucleophiles affording the products in good to excellent yields (up
to 95%) and generally with high regioselectivities (C3:C2 up to >99:1).
C. Wang, H. Yamamoto, J. Am. Chem. Soc., 2014,
136, 6888-6891.
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.
A highly regio- and enantioselective hydroxyamination of aldehydes with in situ
generated nitrosocarbonyl compounds from hydroxamic acid derivatives was
realized by combining TEMPO and BPO as oxidants in the presence of a
binaphthyl-modified amine catalyst.
T. Kano, F. Shirozu, K. Maruoka, J. Am. Chem. Soc., 2013,
135, 17735-17738.
A palladium-catalyzed allylic amination enables an asymmetric synthesis of
α,α-disubstituted allylic N-arylamines from highly modular vinyl cyclic
carbonates and unactivated aromatic amine nucleophiles. The catalytic process
features minimal waste production, high asymmetric induction, and operational
simplicity.
A. Cai, W. Guo, L. Martínez-Rodríguez, A. W. Kleij, J. Am. Chem. Soc., 2016,
138, 14194-14197.