Synthesis of enantiopure dihydropyranones: aldol-based ring expansion of dihydrofurans.

Synthesis of enantiopure dihydropyranones: aldol-based ring expansion of dihydrofurans.

Show other versions (1)

[reaction: see text] The stereoselective Birch reduction of 3-methyl-2-furoic acids using a readily available chiral auxilairy is described; by coupling this process to an oxidative cleavage/aldol ring closure sequence we were able to produce highly functionalized and enantiopure dihydropyranones in...

Descrición completa

Detalles Bibliográficos
Main Authors:	Donohoe, T, Raoof, A, Freestone, G, Linney, I, Cowley, A, Helliwell, M
Formato:	Journal article
Idioma:	English
Publicado:	2002

Títulos similares

Synthesis of enantiopure dihydropyranones: Aldol-based ring expansion of dihydrofurans.
por: Freestone, G, et al.
Publicado: (2003)

ORGN 558-Formation of enantiopure pyrroline building blocks for natural product synthesis
por: Thomas, R, et al.
Publicado: (2006)

Partial reduction of annulated heterocycles as a general route to medium rings containing oxygen and nitrogen.
por: Donohoe, T, et al.
Publicado: (2001)

Palladium-catalyzed oxidative cyclizations: synthesis of dihydropyranones and furanones.
por: Reiter, M, et al.
Publicado: (2005)

Reductive aldol reactions on aromatic heterocycles
por: Donohoe, T, et al.
Publicado: (2000)

A catalytic asymmetric bioorganic route to enantioenriched tetrahydro- and dihydropyranones.
por: Baker-Glenn, C, et al.
Publicado: (2005)

Asymmetric synthesis of aldol products derived from unsymmetrical ketones: assignment of the absolute configuration of antibody aldol products
por: Maggiotti, V, et al.
Publicado: (2002)

Substituted alkenediols by alkylative double ring opening of dihydrofuran and dihydropyran epoxides.
por: Hodgson, D, et al.
Publicado: (2001)

The asymmetric synthesis of (S,S)-methylphenidate hydrochloride via ring-opening of an enantiopure aziridinium intermediate with phenylmagnesium bromide
por: Davies, S, et al.
Publicado: (2019)

Enantiopure lithium amides in asymmetric synthesis
por: Lv, L
Publicado: (2013)

Intramolecular hydride addition to pyridinium salts: new routes to enantiopure dihydropyridones.
por: Donohoe, T, et al.
Publicado: (2011)

Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters.
por: Dixon, D, et al.
Publicado: (2001)

An Efficient Synthesis of Enantiopure (R)-heteroarylpyrimidine Analogs
por: Guo-Ming Zhao, et al.
Publicado: (2013-09-01)

A short synthesis of an enantiopure benzo[e]isoindolinone
por: Andrews, MD, et al.
Publicado: (1997)

Enantiopure oxazolidinones as chiral acids in the asymmetric protonation of N-Boc pyrrole derived enolates.
por: Carbery, DR, et al.
Publicado: (2004)

Organolithium-induced synthesis of unsaturated diols from epoxides of dihydrofurans and dihydropyrans
por: Hodgson, D, et al.
Publicado: (2002)

Five-membered ring annelation in [2.2]paracyclophanes by aldol condensation
por: Henning Hopf, et al.
Publicado: (2014-08-01)

Diastereoselective reductive aldol reactions of Boc-protected electron deficient pyrroles
por: Donohoe, T, et al.
Publicado: (2003)

Scope of the reductive aldol reaction: application to aromatic carbocycles and heterocycles.
por: Donohoe, T, et al.
Publicado: (2003)

Synthesis of densely functionalized enantiopure indolizidines by ring-closing metathesis (RCM) of hydroxylamines from carbohydrate-derived nitrones
por: Marco Bonanni, et al.
Publicado: (2007-12-01)

Oxidative cyclization of diols derived from 1,5-dienes: Formation of enantiopure cis-tetrahydrofurans by using catalytic osmium tetroxide; Formal synthesis of (+)-cis-solamin
por: Donohoe, T, et al.
Publicado: (2005)

Oxidative cyclization of diols derived from 1,5-dienes: formation of enantiopure cis-tetrahydrofurans by using catalytic osmium tetroxide; formal synthesis of (+)-cis-solamin.
por: Donohoe, T, et al.
Publicado: (2005)

Synthesis of dihydrofurans using nano-CuFe2O4@Chitosan
por: Javad Safaei-Ghomi, et al.
Publicado: (2017-09-01)

Oxidation products of 2-acyl-4,5-dihydrofurans
por: Robertson, J, et al.
Publicado: (2006)

Intermediates in the intermolecular, asymmetric Heck arylation of dihydrofurans
por: Hii, K, et al.
Publicado: (1997)

Synthesis of novel enantiopure ionic liquids from (S)-malic acid
por: Marco Bonanni, et al.
Publicado: (2013-09-01)

Alcohol Dehydrogenases with anti‐Prelog Stereopreference in Synthesis of Enantiopure Alcohols
por: Prof. Dr. Musa M. Musa
Publicado: (2022-04-01)

Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives
por: Paola Bonaccorsi, et al.
Publicado: (2013-11-01)

Chemoenzymatic synthesis of enantiopure dihydroxy-1,2,3,4-tetrahydronaphthalenes
por: Derek R. Boyd, et al.
Publicado: (2003-04-01)

Convenient synthesis of enantiopure cyclic alpha-hydroxyalkyl alpha-amino esters
por: Andrews, MD, et al.
Publicado: (1996)

Lewis Acid-Catalyzed 2,3-Dihydrofuran Acetal Ring-Opening Benzannulations toward Functionalized 1-Hydroxycarbazoles
por: Shaoren Yuan, et al.
Publicado: (2022-11-01)

Enantiopure bicyclic piperidinones: Stereocontrolled cycloadditions
por: Brewster, A, et al.
Publicado: (2005)

Synthesis of furan substituted dihydrofuran compounds by radical cyclization reactions mediated by manganese(III) acetate
por: Mehmet Yılmaz, et al.
Publicado: (2014-08-01)

Intramolecular aldol ring closures of cysteine derivatives leading to densely functionalised pyroglutamates
por: Almahli, H, et al.
Publicado: (2019)

Synthesis of cyclohexanone and chalcone derivative by mixed aldol condensation /
por: 279336 Aisyah Mohamad Sharif, et al.
Publicado: (2005)

Doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure N-enoyl oxazolidin-2-ones: a mechanistic probe
por: Davies, S, et al.
Publicado: (2010)

Comparison of L-Threonine Aldolase Variants in the Aldol and Retro-Aldol Reactions
por: Kateryna Fesko
Publicado: (2019-05-01)

A short synthesis of aphanamol I in both racemic and enantiopure forms
por: Burton, J, et al.
Publicado: (2016)

Natural product inspired organic synthesis: enantiopure heterocycles modelled on pramanicin
por: Tan, S
Publicado: (2014)

Garner’s aldehyde as a versatile intermediate in the synthesis of enantiopure natural products
por: Mikko Passiniemi, et al.
Publicado: (2013-11-01)