Online citations, reference lists, and bibliographies.
← Back to Search

A Highly Enantioselective Amino Acid-catalyzed Route To Functionalized α-amino Acids

A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. Barbas
Published 2002 · Chemistry

Save to my Library
Download PDF
Analyze on Scholarcy Visualize in Litmaps
Share
Reduce the time it takes to create your bibliography by a factor of 10 by using the world’s favourite reference manager
Time to take this seriously.
Get Citationsy
The development of syntheses providing enantiomerically pure α-amino acids has intrigued generations of chemists and been the subject of intense research. This report describes a general approach to functionalized α-amino acids based on catalytic asymmetric synthesis. Proline catalyzed Mannich-type reactions of N-PMP-protected α-imino ethyl glyoxylate with a variety of unmodified ketones to provide functionalized α-amino acids in high yields with excellent regio-, diastereo-, and enantioselectivities. Study of seven examples yielded six with product ee values of ≥99%. In reactions involving ketone donors where diastereoisomeric products could be formed, two adjacent stereogenic centers were created simultaneously upon carbon−carbon bond formation with complete syn-stereocontrol. Significantly, this methodology utilizes readily available and rather inexpensive starting materials, does not require any preactivation of substrates or metal ion assistance, and can be carried out on a gram scale under operation...



This paper is referenced by
10.1016/J.TET.2021.132225
Synthesis of alkynyl Z-ketimines and their application in amine-catalyzed asymmetric Mannich reactions and conjugate addition
C. Homma (2021)
10.1039/d0ob01722a
Total synthesis and absolute structure of N55, a positive modulator of GLP-1 signaling.
Nai-Pin Lin (2020)
10.1021/acs.orglett.0c00824
Synthesis of Tetramic Acid Derivatives via a Tandem Umpolung Alkylation/Reduction/Cyclization Reaction of γ-Hydrazono β-Ketoester.
Isao Mizota (2020)
10.1039/c9nj05114g
An umpolung reaction of α-iminonitriles and its application to the synthesis of aminomalononitriles
M. Shimizu (2020)
10.1039/d0sc05269h
Construction of chiral α-tert-amine scaffolds via amine-catalyzed asymmetric Mannich reactions of alkyl-substituted ketimines†
C. Homma (2020)
10.1039/d0ob01989e
Synthesis of Mannich-type derivatives from amides activated by hydrogen bonding with ZnCl2.
Zhi‐Yu Hu (2020)
10.1002/chem.202001514
Prebiotically Plausible Organocatalysts Enabling a Selective Photoredox α‐Alkylation of Aldehydes on the Early Earth
Anna C. Closs (2020)
10.1080/00304948.2020.1805995
Ultrasound-Promoted One-Pot Three-Component Synthesis of β–Amino Carbonyl Compounds Using Manganese Perchlorate
B. Kaur (2020)
10.1002/jhet.4015
Electrophilic amination reactions with 1 H ‐indazole ‐3‐carboxylates: Synthesis of amino acid frameworks and 3‐amino ‐2‐oxindoles
Isao Mizota (2020)
10.1039/C9RA04889H
Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products
M. Shimizu (2019)
10.1002/chem.201903552
Control of Chemical Reactions Using Molecules that Buffer Non-aqueous Solutions.
Muhammad Sohail (2019)
10.1016/J.TETLET.2019.03.031
Anti-selective direct asymmetric Mannich reaction catalyzed by protease
Yu-Jue Chen (2019)
10.3390/molecules24071216
The Asymmetric A3(Aldehyde–Alkyne–Amine) Coupling: Highly Enantioselective Access to Propargylamines
Jia-Nan Mo (2019)
10.1016/J.TETLET.2018.01.054
A convenient one-pot approach to Paclitaxel (Taxol) side chain via 1,3-dipolar cycloaddition of carbonyl ylides and N-benzoylbenzyl imines
Jiajun Sheng (2018)
10.1016/j.ultsonch.2018.07.012
Sono-synthesis approach of reduced graphene oxide for ammonia vapour detection at room temperature.
Pandiyarasan Veluswamy (2018)
10.3139/113.110566
Synthesis of 4-Hydroxy-4-(4-nitrophenyl)butan-2-one using p-Nitro Benzaldehyde and Acetone in Aqueous Micellar Media using L-Proline
S. Mandal (2018)
10.1002/slct.201702483
Organocatalyzed Synthesis of Medicinally Important Chromeno[2, 3-d]pyrimidine-triones in Biodegradable Reaction Medium
P. Rai (2018)
10.1016/j.tet.2018.09.006
Enantioselective anti-Mannich reaction catalyzed by modularly designed organocatalysts.
Swapna Konda (2018)
10.14288/1.0372310
Bicyclic octapeptide alpha-Amanitin, the death cap mushroom toxin : the total synthesis and derivatives of the hydroxyproline residue
Kaveh Matinkhoo (2018)
10.1021/acs.orglett.7b01676
Determination of Relative Frequency of Carbanion Formation at α-Positions of Ketones under Aldol Reaction Catalysis Conditions.
Dongxin Zhang (2017)
10.1007/S13369-017-2615-Y
Synthesis of 1,2-Diamino Acid Derivatives Utilizing Diastereoselective Tandem N-Alkylation/Homo- and Cross-Addition Reaction of $$\alpha $$α-Aldimino Thioesters
Isao Mizota (2017)
10.1002/anie.201708103
Enantioselective Direct Mannich-Type Reactions Catalyzed by Frustrated Lewis Acid/Brønsted Base Complexes.
Ming Shang (2017)
10.1246/BCSJ.20160402
Synthesis of δ-Lactone and Amino Acid Frameworks Utilizing the Umpoled Reactivity of β,γ-Alkenyl α-Iminoester
M. Kawanishi (2017)
10.1016/J.CCLET.2016.06.053
Enantioselective trapping of oxonium ylide intermediates by N-benzhydryl-α-imino ester: Synthesis of β-tetrasubstituted α-amino acids
Shi-Kun Jia (2017)
10.1021/acs.joc.7b01274
In Situ-Generated Glycinyl Chloroaminals for a One-Pot Synthesis of Non-proteinogenic α-Amino Esters.
Shyam S. Samanta (2017)
10.1002/9780471264194.FOS02343.PUB6
Chiral Auxiliaries and Catalysts
T. Ho (2017)
10.1002/chem.201600635
Development of a syn-Selective Mannich Reaction of Aldehydes with Propargylic Imines by Dual Catalysis: Asymmetric Synthesis of Functionalized Propargylic Amines.
Irati Lapuerta (2016)
10.1002/tcr.201500267
Umpolung Reactions of α-Imino Esters: Useful Methods for the Preparation of α-Amino Acid Frameworks.
Isao Mizota (2016)
10.1515/ASORG-2015-0001
Solvent-controlled diastereoselectivity in tryptophan-catalyzed Mannich reactions
G. Valero (2015)
10.1002/QUA.24859
Density functional study of organocatalytic mannich‐type reactions: Insight into reverse diastereoselectivities arising from catalysts with different scaffolds
C. Tian (2015)
10.1016/J.TETLET.2014.11.054
Synthetic study on dolastatin 16: concise and scalable synthesis of two unusual amino acid units
Taiki Umezawa (2015)
10.1007/978-3-319-17593-5_2
Total Synthesis of Carbohydrates
Rainer Mahrwald (2015)
See more
Semantic Scholar Logo Some data provided by SemanticScholar