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

Enantioselective Addition Of Diethylzinc To Benzaldehyde Catalyzed By A Small Amount Of Chiral 2-amino-1-alcohols

N. Oguni, Takao Omi
Published 1984 · Chemistry

Cite This
Download PDF
Analyze on Scholarcy
Share
Abstract The reaction of diethylzinc with benzaldehyde catalyzed by a small amount of chiral 2-amino-1-alcohols in toluene at room temperature gave optically active 1-phenylpropan-1-ol almost quantitatively in ∼, 50% ee.
This paper references



This paper is referenced by
10.1002/9783527675142.CH10
Bifunctional Lewis Base Catalysis with Dual Activation of R–M and C=O (n → σ*)
M. Hatano (2016)
10.1016/J.TETASY.2004.09.031
Synthesis of a C2-symmetric chiral bipyridyldiol ligand and its application in the enantioselective addition of diethylzinc to substituted benzaldehydes
Yi-Jing Chen (2004)
10.1002/anie.201204579
Catalytic asymmetric synthesis of allylic alcohols and derivatives and their applications in organic synthesis.
A. Lumbroso (2013)
10.1016/B978-0-08-095167-6.00325-6
3.25 Stoichiometric Auxiliary Ligands for Metals and Main Group Elements: Ligands for Zinc
A. Charette (2012)
10.1016/J.TETASY.2006.07.028
The effect of direct steric interaction between substrate substituents and ligand substituents on enantioselectivities in asymmetric addition of diethylzinc to aldehydes catalyzed by sterically congested ferrocenyl aziridino alcohols
Min-Can Wang (2006)
10.1002/9781118484722.CH2
Organomagnesium and Organozinc Chemistry
Paul Knochel (2013)
10.1007/978-3-642-15334-1_5
Formation of C-C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation.
John F Bower (2011)
10.1246/CL.1996.343
Enantioselective Addition of Diethylzinc to Aldehydes Using 1, 1′-Bi-2-naphthol-3, 3′-dicarboxamide as a Chiral Auxiliary
H. Kitajima (1996)
10.1039/FT9949001789
Theoretical studies of nucleophilic additions of monomeric and dimeric organometallics
Masaharu Nakamura (1994)
10.1002/CJOC.201090036
Chirality Control by Substituents in the Asymmetric Addition of Et2Zn to Aromatic Aldehydes Catalyzed by cis‐(1R,2S)‐2‐Benzamidocyclohexanecarboxylic Acid Derived 1,3‐Aminoalcohols
Xiangbo Wang (2010)
10.1016/J.TETLET.2014.10.101
A new pyrrolidine-derived atropisomeric amino alcohol as a highly efficient chiral ligand for the asymmetric addition of diethylzinc to aldehydes
Ferenc Faigl (2014)
10.1016/J.TETASY.2005.12.011
Enantioselective addition of diethylzinc to aldehydes catalyzed by γ-amino alcohols derived from (+)- and (−)-α-pinene
Zsolt Szakonyi (2006)
10.1016/S0957-4166(02)00183-0
trans-(1S,2S)-1-Substituted-2-(N,N-dialkylamino)-1-indanol derivatives as chiral ligands in the catalytic enantioselective addition of diethylzinc to aldehydes
Qianyong Xu (2002)
10.1016/S0040-4020(01)90463-6
Highly enantioselective addition of primary alkyl Grignard reagents to carbocyclic and heterocyclic arylketones in the presence of magnesium TADDOLate preparative and mechanistic aspects
B. Weber (1994)
10.1016/S0040-4039(00)96695-4
Chiral catalysts for the enantioselective addition of organometallic reagents to aldehydes
E. Corey (1987)
10.1002/HC.20076
Synthesis of chiral hydroxythiolanes as potential catalysts for asymmetric organozinc additions to carbonyl compounds
P. Kiełbasiński (2005)
10.1016/S0040-4039(00)80834-5
Enantioselective synthesis of sec-allylalcohols by catalytic asymmetric addition of divinylzinc to aldehydes.
W. Oppolzer (1988)
10.1016/J.TET.2011.02.042
Commercially available neat organozincs as highly reactive reagents for catalytic enantioselective addition to ketones and aldehydes under solvent free conditions
M. Hatano (2011)
10.1016/B978-0-08-095167-6.00310-4
3.10 Alkaloid-Derived Auxiliaries: Ephedra Alkaloids
Shawn R. Hitchcock (2012)
10.1016/J.TET.2004.07.015
Bifunctional pyridyl alcohols with the bicyclo[3.3.0]octane scaffold in the asymmetric addition of diethylzinc to aldehydes
Y. Zhong (2004)
10.1016/S0957-4166(00)82246-6
Chiral diethanolamines and their lithium alcoholates as catalysts in the enantioselective alkylation of benzaldehyde by diethylzinc.
E. D. Vries (1993)
10.1002/ANGE.201204579
Katalytische asymmetrische Synthese von Allylalkoholen und Allylalkohol‐Derivaten und deren Anwendung in der organischen Synthese
A. Lumbroso (2013)
10.1021/ar500020k
Asymmetric Functional Organozinc Additions to Aldehydes Catalyzed by 1,1′-Bi-2-naphthols (BINOLs)†
L. Pu (2014)
10.1016/S0957-4166(97)00480-1
Viable use of 2-substituted thiazolidine-4-methanol diastereoisomeric mixtures during asymmetric borane reduction of aromatic ketones
M. Calmès (1997)
10.1021/ol401425s
Catalytic asymmetric aldol-type reaction of zinc enolate equivalent of amides.
Ryosuke Haraguchi (2013)
10.1016/B0-08-045047-4/00111-4
Zinc and Cadmium
P. Knochel (2007)
10.1038/342631A0
Chemical asymmetric synthesis
J. M. Brown (1989)
10.1016/S0040-4039(00)96696-6
Zinc complexes of chiral phenols as catalysts for enantioselective addition of organozinc reagents to aldehydes
E. Corey (1987)
10.1016/0040-4039(96)00955-0
Tellurium-zinc exchange reaction. A new preparative method of alkenylzinc reagents
J. Terao (1996)
10.1246/BCSJ.20120105
Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by (S)-1-Alkyl-2-(arylamino)methylpyrrolidine
Naoya Hosoda (2012)
10.1016/J.TET.2012.11.025
C2 symmetrical nickel complexes derived from α-amino amides as efficient catalysts for the enantioselective addition of dialkylzinc reagents to aldehydes
J. Escorihuela (2013)
10.1016/J.TET.2015.07.031
Enantioselective addition of diethylzinc to aldehydes catalyzed by (R)-1-phenylethylamine-derived 1,4-amino alcohols
Masatoshi Asami (2015)
See more
Semantic Scholar Logo Some data provided by SemanticScholar