Asymmetric synthesis of alpha-alkylated aldehydes using terminal epoxide-derived chiral enamines.

Asymmetric synthesis of alpha-alkylated aldehydes using terminal epoxide-derived chiral enamines.

(Chemical Equation Presented) Effective discrimination: Efficient lithium amide-induced terminal epoxide-enamine transformation provides the first enamines capable of generating α-alkylated aldehydes with high asymmetric induction by intermolecular nucleophilic substitution (see scheme). © 2008 Wile...

Volledige beschrijving

Bibliografische gegevens
Hoofdauteurs:	Hodgson, D, Kaka, N
Formaat:	Journal article
Taal:	English
Gepubliceerd in:	John Wiley and Sons 2008

Gelijkaardige items

Asymmetric synthesis of α-alkylated aldehydes using chiral enamines
door: Kaka, N, et al.
Gepubliceerd in: (2008)

Enantioenriched a-substituted aldehydes via diastereoselective enamine alkylation
door: Kaka, N, et al.
Gepubliceerd in: (2007)

Synthesis and C-alkylation of hindered aldehyde enamines.
door: Hodgson, D, et al.
Gepubliceerd in: (2009)

C-alkylation of chiral tropane- and homotropane-derived enamines.
door: Hodgson, D, et al.
Gepubliceerd in: (2013)

Enamines from terminal epoxides and hindered lithium amides.
door: Hodgson, D, et al.
Gepubliceerd in: (2004)

Transition states and origins of 1,4-asymmetric induction in alkylations of 2,2,6-trialkylpiperidine enamines.
door: Um, J, et al.
Gepubliceerd in: (2010)

Asymmetric Induction in C-Alkylation of Tropane-Derived Enamines: Congruence Between Computation and Experiment
door: Li, Y, et al.
Gepubliceerd in: (2017)

Synthesis of planar chiral ferrocenyl sulfides and evaluation as catalysts for the asymmetric epoxidation of aldehydes
door: Stéphanie Minière, et al.
Gepubliceerd in: (2005-01-01)

CHIRAL SUCCINATE ENOLATE EQUIVALENTS FOR THE ASYMMETRIC-SYNTHESIS OF ALPHA-ALKYL SUCCINIC ACID-DERIVATIVES
door: Bashiardes, G, et al.
Gepubliceerd in: (1989)

Methods for direct generation of alpha-alkyl-substituted aldehydes
door: Hodgson, D, et al.
Gepubliceerd in: (2014)

Studies with enamines: Functionally substituted enamines as aldehyde equivalents in Gewald reaction
door: Saleh Al-Mousawi, et al.
Gepubliceerd in: (2007-11-01)

First direct deprotonation-electrophile trapping of simple epoxides: synthesis of alpha,beta-epoxysilanes from terminal epoxides.
door: Hodgson, D, et al.
Gepubliceerd in: (2001)

SuperQuat N-acyl-5,5-dimethyloxazolidin-2-ones for the asymmetric synthesis of alpha-alkyl and beta-alkyl aldehydes.
door: Bull, S, et al.
Gepubliceerd in: (2003)

NiH-catalyzed asymmetric hydroarylation of N-acyl enamines to chiral benzylamines
door: Yuli He, et al.
Gepubliceerd in: (2021-01-01)

Chiral epoxides by desymmetrizing deprotonation of meso-epoxides.
door: Hodgson, D, et al.
Gepubliceerd in: (2002)

Substituted epoxides by lithiation of terminal epoxides.
door: Hodgson, D, et al.
Gepubliceerd in: (2004)

Accessible sugars as asymmetric olefin epoxidation organocatalysts: glucosaminide ketones in the synthesis of terminal epoxides.
door: Boutureira, O, et al.
Gepubliceerd in: (2009)

Asymmetric catalytic hydrogenation of imines and enamines in natural product synthesis
door: Pei Tang, et al.
Gepubliceerd in: (2020-06-01)

Enantioselective synthesis of epoxides by alpha-deprotonation--electrophile trapping of achiral epoxides.
door: Hodgson, D, et al.
Gepubliceerd in: (2003)

Catalytic Asymmetric Amino Acid and Its Derivatives by Chiral Aldehyde Catalysis
door: Kaijin Lin, et al.
Gepubliceerd in: (2021-06-01)

2,5-Disubstituted pyrrolidines: synthesis by enamine reduction and subsequent regioselective and diastereoselective alkylations.
door: Hussaini, SR, et al.
Gepubliceerd in: (2006)

ASYMMETRIC-SYNTHESIS OF DIFFERENTIALLY PROTECTED ALPHA-ALKYL SUCCINATES
door: Bashiardes, G, et al.
Gepubliceerd in: (1989)

Enantioselective alpha-deprotonation of epoxides.
door: Hodgson, D
Gepubliceerd in: (2001)

Methods for direct generation of α-alkyl-substituted aldehydes
door: Hodgson, D, et al.
Gepubliceerd in: (2014)

Methods for direct generation of α-alkyl-substituted aldehydes
door: Hodgson, D, et al.
Gepubliceerd in: (2014)

2,5-Disubstituted pyrrolidines: versatile regioselective and diastereoselective synthesis by enamine reduction and subsequent alkylation.
door: Hussaini, SR, et al.
Gepubliceerd in: (2003)

New Catalytic Asymmetric Strategies to Access Chiral Aldehydes
door: Clément Mazet
Gepubliceerd in: (2011-10-01)

Enantioselective alkylative double ring-opening of epoxides derived from cyclic allylic ethers: synthesis of enantioenriched unsaturated diols.
door: Hodgson, D, et al.
Gepubliceerd in: (2003)

ASYMMETRIC-SYNTHESIS OF SYN-ALPHA-ALKYL-BETA-AMINO ACIDS
door: Davies, S, et al.
Gepubliceerd in: (1994)

ASYMMETRIC-SYNTHESIS OF ANTI-ALPHA-ALKYL-BETA-AMINO ACIDS
door: Davies, S, et al.
Gepubliceerd in: (1994)

ASYMMETRIC-SYNTHESIS OF ANTI-ALPHA-ALKYL-BETA-AMINO CARBOXAMIDES
door: Davies, S, et al.
Gepubliceerd in: (1995)

Enantioselective Synthesis of 2,2-Disubstituted Terminal Epoxides via Catalytic Asymmetric Corey-Chaykovsky Epoxidation of Ketones
door: Shigeki Matsunaga, et al.
Gepubliceerd in: (2012-02-01)

The acid free asymmetric intermolecular α-alkylation of aldehydes in fluorinated alcohols
door: Xiao, Jian, et al.
Gepubliceerd in: (2013)

Asymmetric synthesis of terminal N-tert-butylsulfinyl aziridines from organoceriums and an alpha-chloroimine.
door: Hodgson, D, et al.
Gepubliceerd in: (2008)

THE SYNTHESIS OF SEVERAL CHIRAL PHOSPHORUS REAGENTS AND THEIR APPLICATION IN THE ASYMMETRIC ADDITION OF AROMATIC ALDEHYDES TO DIETHYLZINC
door: Yang, Zhuihong, et al.
Gepubliceerd in: (2001-06-01)

Straightforward synthesis of alpha,beta-epoxysilanes from terminal epoxides by lithium 2,2,6,6-tetramethylpiperidide-mediated deprotonation-in situ silylation
door: Hodgson, D, et al.
Gepubliceerd in: (2002)

Direct asymmetric syntheses of chiral aldehydes and ketones via N-acyl chiral auxiliary derivatives including chiral Weinreb amide equivalents.
door: Davies, S, et al.
Gepubliceerd in: (2013)

Deprotonation-electrophile trapping of terminal epoxides.
door: Hodgson, D, et al.
Gepubliceerd in: (2005)

Intramolecular cyclopropanation of unsaturated terminal epoxides.
door: Hodgson, D, et al.
Gepubliceerd in: (2004)

One-pot synthesis of epoxides from benzyl alcohols and aldehydes
door: Edwin Alfonzo, et al.
Gepubliceerd in: (2018-09-01)