← Back to Search
Highly Regioselective N-alkylation Of Nonracemic Betti Base: A Novel One-pot Synthesis Of Chiral N-methyl-N-alkyl Betti Bases
Yanmei Dong, J. Sun, X. Wang, X. Xu, Liya Cao, Yuefei Hu
Published 2004 · Chemistry
Download PDFAnalyze on Scholarcy
Abstract A novel one-pot preparation of chiral N -methyl- N -alkyl Betti bases has been developed involving a highly regioselective N -alkylation of ( S )-(+)-Betti base. The strategy involved formation-cleavage of the oxazine ring and N -methylation with BtCH 2 OH under neutral conditions.
This paper references
Highly diastereoselective aminoalkylation of naphthols with chiral amines mediated by lithium perchlorate solution in diethyl ether
M. R. Saidi (2003)
Dramatically synergetic effect of carboxylic acid additive on tridentate titanium catalyzed enantioselective hetero-diels-alder reaction: additive acceleration and nonlinear effect.
Y. Yuan (2002)
A convenient, one-step synthesis of optically active tertiary aminonaphthol and its applications in the highly enantioselective alkenylations of aldehydes.
J. Ji (2003)
A practical o-hydroxybenzylamines promoted enantioselective addition of dialkylzincs to aldehydes with asymmetric amplification
G. Palmieri (2000)
To probe the origin of activation effect of carboxylic acid and (+)-NLE in tridentated titanium catalyst systems.
Y. Yuan (2002)
THE BETTI BASE : ABSOLUTE CONFIGURATION AND ROUTES TO A FAMILY OF RELATED CHIRAL NONRACEMIC BASES
C. Cardellicchio (1998)
Novel preparation of non-racemic 1-[α-(1-azacycloalkyl)benzyl]-2-naphthols from Betti base and their application as chiral ligands in the asymmetric addition of diethylzinc to aryl aldehydes
J. Lu (2002)
Asymmetric Syntheses of 2-Substituted and 2,5-Disubstituted Pyrrolidines from (3S,5R,7aR)-5-(Benzotriazol-1-yl)-3-phenyl[2,1-b]oxazolopyrrolidine.
A. Katritzky (1999)
Selective Cross-Coupling of 2-Naphthol and 2-Naphthylamine Derivatives. A Facile Synthesis of 2,2',3-Trisubstituted and 2,2',3,3'-Tetrasubstituted 1,1'-Binaphthyls
M. Smrčina (1994)
2-Substituted-1,2,3,4-tetrahydroisoquinolines and chiral 3-carboxyl analogues from N-benzotriazolylmethyl-N-phenethylamines
A. Katritzky (2001)
An improved synthesis of chiral 1-[α-(1-azacycloalkyl)benzyl]-2-naphthols
X. Xu (2004)
Synthesis of a new type of chiral amino phosphine ligands for asymmetric catalysis
Yi Wang (2002)
Efficient Routes to Chiral 2-Substituted and 2,6-Disubstituted Piperidines
A. R. Katritzky (1998)
Synthesis of chiral ligands derived from the Betti base and their use in the enantioselective addition of diethylzinc to aromatic aldehydes
J. Lu (2002)
Catalytic, Enantioselective Acetone Aldol Additions with 2-Methoxypropene
E. M. Carreira (1995)
Highly Efficient Catalytic Synthesis of α‐Amino Acids under Phase‐Transfer Conditions with a Novel Catalyst/Substrate Pair
Yuri N. Belokon (2001)
The application of chiral aminonaphthols in the enantioselective addition of diethylzinc to aryl aldehydes.
D. Liu (2001)
Solvent-free asymmetric aminoalkylation of electron-rich aromatic compounds: stereoselective synthesis of aminoalkylnaphthols by crystallization-induced asymmetric transformation.
C. Cimarelli (2001)
Use of readily available chiral compounds related to the betti base in the enantioselective addition of diethylzinc to aryl aldehydes
C. Cardellicchio (1999)
A practical stereoselective synthesis of secondary and tertiary aminonaphthols: chiral ligands for enantioselective catalysts in the addition of diethylzinc to benzaldehyde
C. Cimarelli (2002)
Synthesis of N-Alkylated and N-Arylated Derivatives of 2-Amino-2‘-hydroxy-1,1‘-binaphthyl (NOBIN) and 2,2‘-Diamino-1,1‘-binaphthyl and Their Application in the Enantioselective Addition of Diethylzinc to Aromatic Aldehydes†
Štěpán Vyskočil (1998)
Non-symmetrically substituted 1,1'-binaphthyls in enantioselective catalysis.
P. Kočovský (2003)
Catalytic, Enantioselective Dienolate Additions to Aldehydes: Preparation of Optically Active Acetoacetate Aldol Adducts
R. A. Singer (1995)
The continuing magic of benzotriazole: An overview of some recent advances in synthetic methodology
A. Katritzky (1999)
α-t-butyl- and α-i-propyl-ortho-hydroxybenzylamines: Racemic synthesis/resolution and asymmetric synthesis
G. Bernardinelli (2000)
Total Synthesis of Macrolactin A with Versatile Catalytic, Enantioselective Dienolate Aldol Addition Reactions.
Y. Kim (1998)
Synthesis of enantiomerically pure 2,2'-dihydroxy-1,1'-binaphthyl, 2,2'-diamino-1,1'-binaphthyl, and 2-amino-2'-hydroxy-1,1'-binaphthyl. Comparison of processes operating as diastereoselective crystallization and as second order asymmetric transformation
M. Smrčina (1992)
This paper is referenced by
A fast and highly efficient one-pot synthesis of novel isoxazolyl pyrido[2,3-b][1,4]oxazin-2(3H)-ones via Smiles rearrangement using task-specific ionic liquid [HMIm]BF4 as green solvent
Modugu Nagi Reddy (2017)
Synthesis of enantiopure aminonaphthol derivatives under conventional/ultrasonic technique and their ring-closure reaction
Emel Pelit (2016)
Synthesis and crystal structures of chiral ferrocene and ruthenocene substituted aminomethylnaphthols obtained through Betti-condensation
Krasimira Dikova (2019)
Copper-catalyzed regioselective intramolecular oxidative α-functionalization of tertiary amines: an efficient synthesis of dihydro-1,3-oxazines.
Mohit L Deb (2013)
A novel N–O ligand for palladium-catalyzed Mizoroki–Heck reaction in neat water
Yufang Wang (2013)
Recent advances in the synthesis and synthetic applications of Betti base (aminoalkylnaphthol) and bis-Betti base derivatives
Abolfazl Olyaei (2019)
Novel synthesis of 2-naphthol Mannich bases and their NMR behaviour
A. Jha (2006)
Modification of micro-channel filling flow by poly(dimethylsiloxane) surface functionalization with fluorine—Substituted aminonaphthols
G. Cortese (2010)
Metal-free intramolecular α-sp3 C–H oxygenation of tert-amine: An efficient approach to 1,3-oxazines
Mohit L. Deb (2016)
Synthesis of 2,4-Disubstituted-3,4-Dihydro-2H- Naphth[2,1-e][1,3]Oxazines
Zuhal Turgut (2009)
Organocatalytic enantioselective aza-Friedel–Crafts reaction of 2-naphthols with benzoxathiazine 2,2-dioxides
Marc Montesinos-Magraner (2015)
Aqueous-Mediated N-Alkylation of Amines
C. B. Singh (2007)
Synthesis of new 1,3-disubstituted-2,3-dihydro-1H-naphth[1,2e][1,3]oxazines.
Z. Turgut (2007)
Acid promoted CIDT for the deracemization of dihydrocinnamic aldehydes with Betti's base
Goffredo Rosini (2010)
Metal-free new synthesis of 1,3-naphthoxazines via intramolecular cross dehydrogenative-coupling reaction of 1-(α-aminoalkyl)-2-naphthols using hypervalent iodine(III) reagent
Nitin A. Waghmode (2016)
Synthesis of 2,4‐Diaryl‐1,3‐benzoxazines via FeCl3‐Catalyzed Annulation of ortho‐Hydroxyphenyl‐Substituted para‐Quinone Methides with Imidates
J. Zhang (2019)
A new approach to the synthesis of benzylidene derivatives of 1-(α-aminobenzyl)-2-naphthols (Betti bases), promising chiral inductors
V. F. Zheltukhin (2007)
Construction of an all-substituted pyrrolidine derivative with multiple stereogenic centers and Betti-base-derived γ-amino alcohols by [1,2]-Wittig rearrangement
Cai-Yun Wang (2015)
Silica vanadic acid [SiO2–VO(OH)2] as an efficient heterogeneous catalyst for the synthesis of 1,2-dihydro-1-aryl-3H-naphth[1,2-e][1,3]oxazin-3-one and 2,4,6-triarylpyridine derivatives via anomeric based oxidation
M. A. Zolfigol (2015)
Preparation, Reactivity, and Synthetic Utility of Simple Benzotriazole Derivatives
Romaric Gérardy (2015)
Nucleophilic addition of amines to ruthenium carbenes: ortho-(alkynyloxy)benzylamine cyclizations towards 1,3-benzoxazines.
C. González-Rodríguez (2015)
Organocatalytic asymmetric addition of naphthols and electron-rich phenols to isatin-derived ketimines: highly enantioselective construction of tetrasubstituted stereocenters.
Marc Montesinos-Magraner (2015)
Redox-Neutral α-Oxygenation of Amines: Reaction Development and Elucidation of the Mechanism
Matthew T. Richers (2014)
Highly Regioselective N-Alkylation of Nonracemic Betti Base: A Novel One-Pot Synthesis of Chiral N-Methyl-N-alkyl Betti Bases.
Yanmei Dong (2004)
1,3-Oxazines and their Benzo Derivatives
L. Lázár (2008)
Arylation of Azaarylmethylamines with Aryl Chlorides and a NiBr2/NIXANTPHOS-based Catalyst.
Gui Gao (2017)
One-pot solvent-free synthesis of 2,3-dihydro-2-substituted-1H-naphtho[1,2-e][1,3]oxazine derivatives using Fe3O4@nano-cellulose/TiCl as a bio-based and recyclable magnetic nano-catalyst
S. Azad (2018)