Categories: C-C Bond Formation > Nitrogen-containing molecules >
Synthesis of β-Amino Acids and Derivatives
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Mannich-rype reactions of secondary amines, aldehydes and ketene silyl acetals
were efficiently promoted by catalytic amounts of diarylborinic acid esters,
affording β-amino esters selectively with no formation of the corresponding
β-hydroxy esters.
Y. Tanaka, T. Hasui, M. Suginome, Synlett, 2008, 1239-1241.
Aminoboranes are highly efficient and mild iminium ion generators in the
Mannich-type aminative coupling of aldehydes with silyl ketene acetals. The
use of diisopropylaminoboranes enables a three-component Mannich reaction of
free secondary amines with aldehydes and silyl ketene acetals.
M. Suginome, L. Uehlin, M. Murakami, J. Am. Chem. Soc.,
2004,
126, 13196-13197.
An indium triiodide catalyzed deoxygenative functionalization of N-sulfonyl
amides with silyl cyanide or silyl enolates in the presence of hydrosilanes
gives α-cyanoamines and β-aminocarboxyl compounds, respectively.
Y. Inamoto, Y. Kaga, Y. Nishimoto, M. Yasuda, A. Baba, Org. Lett., 2013,
15, 3448-3451.
A preparation of highly substituted β-amino acids involves a Vilsmeier-Haack
reaction with nonaromatic carbon nucleophiles. The reaction enabled the
synthesis of several β2,2,3-amino esters, such as derivatives of
homoproline, homoalanine, and homopipecolinic esters.
A. Roamens, G. Bélanger, Org. Lett.,
2015,
17, 322-325.
A highly efficient Mukaiyama aldol reaction is catalyzed by sodium
phenoxide-phosphine oxides as simple homogeneous Lewis base catalysts, which
minimized competing retro-aldol reaction. Various aromatic ketones and
aldimines, aldol and Mannich-type products with an α-quaternary carbon center
were obtained in good to excellent yields.
M. Hatano, E. Takagi, K. Ishihara, Org. Lett., 2007,
9, 4527-4530.
The Hf(OTf)4-catalyzed Mannich-type reaction of an enol silyl ether
or a ketene silyl acetal with an N,O-acetal allows the preparation of
amino acid derivatives. In particular, use of the N,O-acetal having a
bis(trimethylsilyl)amino group directly produced N-unprotected aspartic acid
derivatives after a standard aqueous workup.
N. Sakai, A. Sato, T. Konakahara, Synlett, 2009,
1449-1452.
Catalytic Silicon-Mediated Carbon-Carbon Bond-Forming Reactions of
Unactivated Amides
S. Kobayashi, H. Kiyohara, M. Yamaguchi, J. Am. Chem. Soc., 2011,
133, 708-711.
Addition of in situ generated samarium acetamide and chloroacetamide enolates to
aldimines afforded 3-aminoamides and 3-amino-2-chloroamides in high yields. A
mechanism is proposed to explain the synthesis and reactivity of samarium
enolates of primary amides.
J. M. Concellón, H. Rodríguez-Solla, C. Concellón, C. Simal, N. Alvaredo, Synlett, 2010,
2119-2121.
N-Benzyldiphenylphosphinamides are deprotonated at the NCα position
diastereospecifically upon treatment with t-BuLi in diethyl ether at low
temperature. Reaction of the anions with various electrophiles and subsequent cleavage of the P-N linkage affords 1,2-amino alcohols and α-, β-, and γ-amino
acids.
P. O. Burgos, I. Fernández, M. J. Iglesias, S. García-Granda, F. L. Ortiz, Org. Lett., 2008,
10, 537-540.
A highly efficient general strategy for the synthesis of 2-amino acids by
homologation of α-amino acids, involving the Reformatsky reaction with a
Mannich-type imminium electrophile is reported.
R. Moumne, S. Lavielle, P. Karoyan, J. Org. Chem., 2006,
71, 3332-3334.
Sonication of diazo ketones derived from Fmoc-protected amino acids in dioxane
in the presence of silver benzoate and water results in clean formation of the
corresponding β-amino acid derivatives. The degree of racemization was examined
using capillary zone electrophoresis. No substantial epimerization occured
except for phenylglycine.
A. Müller, C. Vogt, N. Sewald, Synthesis,
1998, 837-841.
The Arndt-Eistert Reaction in Peptide Chemistry: A Facile Access to
Homopeptides
J. Podlech, D. Seebach, Angew. Chem. Int. Ed.,
1995, 34, 471-472.
A one-pot, three-component reaction between an aromatic aldehyde, an enolizable
ketone or a β-keto ester, and a nitrile in the presence of acetyl chloride is
accomplished efficiently using cyanuric chloride in an aqueous medium to give
the corresponding β-acetamido ketone or ester in high yield.
B. Das, M. Srilatha, B. Veeranjaneyulu, B. R. Rao, Synthesis, 2010,
803-806.
In a highly enantioselective direct Mannich-type reaction of aldimines with
dialkyl malonates, an inexpensive Mg(II)-BINOLate salt can activate both
aldimines and malonates as a cooperative acid-base catalyst. Various
β-aminoesters and α-halo-β-aminoesters could be synthesized in high yields and
with high enantioselectivities even in gram-scale.
M. Hatano, T. Horibe, K. Ishihara, Org. Lett., 2010,
12, 3502-3505.
A highly enantioselective Mannich reaction with in situ generation of
carbamate-protected imines from stable α-amido sulfones catalyzed by an organic
catalyst provides a concise and highly
enantioselective route converting aromatic and aliphatic aldehydes into
optically active aryl and alkyl β-amino acids.
J. Song, H.-W. Shih, L. Deng, Org. Lett., 2007,
9, 603-606.
Li(I) BINOLate salts as Lewis acid-Brřnsted base catalysts offer high catalytic
activity toward 1,3-dicarbonyl compounds such as diketone, ketoester,
ketothioester, ketoamide, and ketolactone. Mannich-type reaction of aldimines
with 1,3-dicarbonyl compounds proceeded at -78 °C within 1-2 h in the presence
of 1−10 mol % catalyst highly enantio- and diastereoselectively.
M. Hatano, T. Horibe, K. Ishihara, J. Am. Chem. Soc., 2010,
132, 56-57.
A base-catalyzed Michael-type addition of sodium diethyl malonate to N-Boc-α-amidoalkyl-p-tolyl
sulfones in tetrahydrofuran followed by hydrolysis of the adducts in refluxing 6
M aqueous hydrochloric acid affords β3-amino acid hydrochlorides in
high yield and excellent purity.
M. Nejman, A. Śliwińska, A. Zwierzak, Tetrahedron, 2005,
61, 8536-8541.
Efficient carbon-carbon bond formation of N-carbobenzyloxy amines
with 1,3-dicarbonyl compounds at the α-position of nitrogen was established
by a one-pot oxidative Mannich reaction using N-tert-butylbenzenesulfinimidoyl
chloride as an oxidant.
J-I. Matsuo, Y. Tanaki, H. Ishibashi, Org. Lett.,
2006,
8, 4371-4374.
The intriguing Rh2(OAc)4 and chiral Brřnsted acid
cocatalyzed three-component Mannich-type reaction of a diazo compound, a
carbamate, and an imine provides rapid and efficient access to both syn-
and anti-α-substituted α,β-diamino acid derivatives with a high level
control of chemo-, diastereo-, and enantioselectivity.
J. Jiang, H.-D. Xu, J.-B. Xi, B.-Y. Ren, F.-P. Lv, X. Guo, L.-Q. Jiang, Z.-Y.
Zhang, W.-H. Hu, J. Am. Chem. Soc., 2011,
133, 8428-8431.
Catalytic asymmetric direct Mannich-type reactions of α-substituted
nitroacetates using a new bench-stable homodinuclear Ni2-Schiff base
complex gave Mannich products in high ee, that serve as precursors for anti-α,β-diamino
acids with an α-tetrasubstituted carbon stereocenter. The Ni complex was also
applicable to direct Mannich-type reactions of malonates and β-keto ester.
Z. Chen, H. Morimoto, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc., 2008,
130, 2170-2171.
An axially chiral dicarboxylic acid has been applied to a highly
enantioselective Mannich reaction of arylaldehyde N-Boc imines and diazo
compounds as a new class of chiral hydrogen-bonding catalyst.
T. Hashimoto, K. Maruoka, J. Am. Chem. Soc., 2007,
129, 10054-10055.
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