Categories: C-N Bond Formation > Amines > Synthesis of primary amines >
Synthesis of protected primary amines
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 carbamates |
 sulfonamides |
Recent Literature
A low catalyst loading of [Cp*IrCl2]2 in the presence of
t-BuOK enables a simple and versatile N-alkylation of sulfonamides with
various alcohols based on a catalytic hydrogen transfer reaction. Various
N-alkylated sulfonamides were prepared in good to excellent yields. Key
catalytic species is a sulfonylimido-bridged unsaturated diiridium complex [(Cp*Ir)2(μ-NTs)2].
M. Zhu, K.-i. Fujita, R. Yamaguchi, Org. Lett., 2010,
12, 1336-1339.
A new, simple method for the conversion of alcohols to tosylamides is
presented.
M. C. Marcotullio, V. Campagna, S. Sternativo, F. Costantino, M. Curini,
Synthesis, 2006, 2760-2766.
A three-component condensation of aldehydes, benzyl carbamate and
allyltrimethylsilane, which affords corresponding protected homoallylic amines
in excellent yields, is catalyzed by iodine.
P. Phukan, J. Org. Chem., 2004, 69, 4005-4006.
An efficient palladium-catalyzed asymmetric amination of 2,3-allenyl
phosphates with nitrogen nucleophiles such as amines, hydroxylamines, and
imides can be performed in presence of SEGPHOS or MeOBIPHEP ligand,
affording the corresponding optically active 1-aminated derivatives with
high enantiomeric excess.
Y. Imada, M. Nishida, K. Kutsuwa, S.-I. Murahashi, T. Naota, Org. Lett.,
2005,
7, 5837-5839.
Iridium-catalyzed allylation of potassium trifluoroacetamide or the highly
reactive ammonia equivalent lithium di-tert-butyliminodicarboxylate forms
a range of conveniently protected, primary, α-branched allylic amines in high
yields, high branched-to-linear regioselectivities, and high enantiomeric excess.
M. J. Pouy, A. Leitner, D. J. Weix, S. Ueno, J. F. Hartwig, Org. Lett., 2007,
9, 3949-3952.
Hydroamination of substituted allenes with benzyl carbamate catalyzed by (NHC)AuCl and AgOTf in dioxane led to isolation
of allylic carbamates in good yield as single
regio- and diastereomers.
R. E. Kinder, Z. Zhang, R. A. Widenhoefer, Org. Lett.,
2008,
10, 3157-3159.
A mild, gold(I)-catalyzed hydroamination of 1,3-dienes is reported. Various
carbamates and sulfonamides add to conjugated dienes to affort protected
allylic amines in good to high yields.
C. Brouwer, C. He, Angew. Chem. Int. Ed., 2006,
45, 1744-1747.
Addition of sulfonamides to alkenes and conjugated dienes can be carried out
using a low catalytic amount of (triphenyl phosphite)gold(I) chloride and silver
triflate under thermal or microwave conditions and at r.t. in the case of
dienes. Terminal alkenes undergo regioselective hydroamination at the internal
carbon atom and dienes at the less substituted double bond.
X. Giner, C. Nájera, Org. Lett.,
2008,
10, 2919-2922.
Ph3PAuOTf catalyzes efficient intra- and intermolecular
hydroamination of unactivated olefins with sulfonamides.
J. Zhang, C.-G. Yang, C. He, J. Am. Chem. Soc.,
2006,
128, 1798-1799.
Copper(II) trifluoromethanesulfonate catalyzed a mild amidation of cyclic ethers
with iminoiodanes with good yields and selectivity. A subsequent reductive
ring-opening of the tosylamidated products gives α,ϖ-amino alcohols.
L. He, J. Yu, J. Zhang, X.-Q. Yu, Org. Lett., 2007,
9, 2277-2280.
An
efficient amidation reaction of saturated C-H bonds catalyzed by a unique
disilver(I) complex is reported. The reaction is stereospecific and
practical for the construction of amine-containing molecules.
Y. Cui, C. He, Angew. Chem. Int. Ed., 2004, 43,
4210-4212.
Y. Cui, C. He, Angew. Chem. Int. Ed., 2004, 43, 4210-4212.
Benzylic hydrocarbons are selectively converted to the corresponding
sulfonamides by the [Cu(CH3CN)4]PF6-catalyzed reaction with anhydrous
TolSO2NNaCl (chloramine-T). Under the same conditions, representative ethers
and olefins are
also amidated.
R. Bhuyan, K. M. Nicholas, Org. Lett., 2007,
9, 3957-3959.
A highly chemoselective PPh3-catalyzed three-component reaction of an
imine, alkyl vinyl ketone, and phthalimide or succinimide gives various highly
functional adducts with high diastereoselectivities via
aza-Morita-Baylis-Hillman reactions of aryl-substituted imines and alkyl vinyl
ketones followed by Michael additions of imides and then epimerization.
S.-e. Syu, Y.-T. Lee, Y.-J. Jang, W. Lin, J. Org. Chem., 2011,
76, 2888-2891.
A new procedure for aminobromination of olefins gives vicinal bromoamine derivatives in high yields using Cu, Mn, or V
catalysts with
p-toluenesulfonamide as nitrogen source and N-bromosuccinimide
(NBS) as bromine source. Excellent regio- and stereoselectivity is shown for different olefinic substrates as well as transition metal
catalysts.
V.
V. Thakur, S. K. Talluri, A. Sudalai, Org. Lett., 2003, 5,
861-864.
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