Highly diastereoselective ketone aldol reactions of butane-2,3-diacetal desymmetrised glycolic acid

Highly diastereoselective ketone aldol reactions of butane-2,3-diacetal desymmetrised glycolic acid

Butane-2,3-diacetal (BDA) desymmetrised glycolic acid building block 1 undergoes highly diastereoselective lithium enolate ketone aldol reactions with a range of methyl and mono-substituted methyl ketones to yield, after acid-catalysed deprotection, enantiopure α,β-dihydroxy acid derivatives bearing...

Disgrifiad llawn

Manylion Llyfryddiaeth
Prif Awduron:	Dixon, D, Guarna, A, Ley, S, Polara, A, Rodriguez, F
Fformat:	Journal article
Iaith:	English
Cyhoeddwyd:	2002

Eitemau Tebyg

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

Studies on the generation of enolate anions from butane-2,3-diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides
gan: Ley, S, et al.
Cyhoeddwyd: (2004)

Studies on the generation of enolate anions from butane-2,3-diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides.
gan: Ley, S, et al.
Cyhoeddwyd: (2004)

Michael, Michael-aldol and Michael-Michael reactions of enolate equivalents of butane-2,3-diacetal protected glycolic acid derivatives.
gan: Ley, S, et al.
Cyhoeddwyd: (2005)

Highly diastereoselective Michael addition reactions of butane-2,3-diacetal desymmetrized glycolic acid. Preparation of alpha-hydroxy-gamma-amino acid derivatives.
gan: Dixon, D, et al.
Cyhoeddwyd: (2001)

Synthesis of a ceramide sphingolipid as a potential sex pheromone of the hair crab Erimacrus isenbeckii using butane-2,3-diacetal desymmetrised glycolic acid building blocks
gan: Dixon, D, et al.
Cyhoeddwyd: (2005)

The use of butane diacetals of glycolic acid as precursors for the synthesis of the phytotoxic calmodulin inhibitor herbarumin II
gan: Diez, E, et al.
Cyhoeddwyd: (2003)

Preparation of desymmetrised meso-tartrate derivatives - synthesis and utility of (R ',R ',R,S)-2,3-butane diacetal protected dimethyl tartrate
gan: Dixon, D, et al.
Cyhoeddwyd: (1999)

Total synthesis of the phytotoxic agent herbarumin II using butane diacetals of glycolic acid as building blocks
gan: Diez, E, et al.
Cyhoeddwyd: (2003)

Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to alpha-hydroxyacid and amide derivatives.
gan: Ley, S, et al.
Cyhoeddwyd: (2004)

New building blocks for efficient and highly diastereoselective polyol production - Synthesis and utility of (R ',R ',S,S) and (S ',S ',R,R)-2,3-butane diacetal protected butane tetrol derivatives
gan: Barlow, J, et al.
Cyhoeddwyd: (1999)

Butane-2,3-diacetal-desymmetrized glycolic acid—a new building block for the stereoselective synthesis of enantiopure α-hydroxy acids
gan: Díez, E, et al.
Cyhoeddwyd: (2001)

The total synthesis of (+)-aspicilin using 2,3-butane diacetal protected butane tetrols via a chiral memory protocol
gan: Dixon, D, et al.
Cyhoeddwyd: (2001)

A new family of cinchona-derived amino phosphine precatalysts: application to the highly enantio- and diastereoselective silver-catalyzed isocyanoacetate aldol reaction.
gan: Sladojevich, F, et al.
Cyhoeddwyd: (2011)

Double diastereoselective SuperQuat glycolate aldol reactions: application to the asymmetric synthesis of polyfunctionalised lactones.
gan: Davies, S, et al.
Cyhoeddwyd: (2004)

A general and efficient procedure for the preparation of enantiopure anti-1,2-diols - synthesis and utility of (R ',R ',S,R)-2,3-butane diacetal protected butane tetrol
gan: Dixon, D, et al.
Cyhoeddwyd: (1999)

Enantioselectivity in the boron aldol reactions of methyl ketones.
gan: Goodman, J, et al.
Cyhoeddwyd: (2007)

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

Rapid assembly of anti,anti-1,2,3-triol motifs via stereoselective addition of organometallics to aldehydes obtained from (R ',R ',S,R)-2,3-butane diacetal protected butanetetraol derivatives
gan: Dixon, D, et al.
Cyhoeddwyd: (2001)

Enantioselective desymmetrisation
gan: Willis, M
Cyhoeddwyd: (1999)

Halogeno Aldol Reaction of Ethyl Vinyl Ketone and Aldehydes Mediated by Titanium Tetrachloride
gan: Guigen Li, et al.
Cyhoeddwyd: (2000-12-01)

Diastereoselective reduction of cyclic bioactive Mannich ketones
gan: Tamás Lóránda, et al.
Cyhoeddwyd: (2003-11-01)

A direct catalytic and diastereoselective aldol route to protected alpha,beta-dihydroxyketones
gan: Willis, M, et al.
Cyhoeddwyd: (2004)

Desymmetrisation of 1,3-diols and their diacetates under enzymatic heterogeneous catalysis and synthesis of 1,3-diols under continuous flow conditions
gan: Pamarthy, Varsha Siri
Cyhoeddwyd: (2019)

An unexpected Prins desymmetrisation reaction driven by silyl migration
gan: Michael Butters, et al.
Cyhoeddwyd: (2012-08-01)

Decarboxylative ketone aldol reactions: development and mechanistic evaluation under metal-free conditions.
gan: Blaquiere, N, et al.
Cyhoeddwyd: (2009)

Bismuth Oxychloride as an Efficient Heterogeneous Catalyst for Aldol Condensation Reaction between Aldehydes and Ketones
gan: Nguyen Thi Kim Oanh, et al.
Cyhoeddwyd: (2023-07-01)

An efficient RuIII/BINAP catalytic system for the aldol reactions of ketones with various aldehydes
gan: Khalil Tabatabaeian, et al.
Cyhoeddwyd: (2010-06-01)

Enantioselective desymmetrisation of achiral epoxides
gan: Hodgson, D, et al.
Cyhoeddwyd: (1996)

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

Production of Methyl Ethyl Ketone from N-Butane
gan: Adil A Al-Hemiri, et al.
Cyhoeddwyd: (2001-12-01)

Consecutive Three- and Four-Component Coupling Reactions with Anions Generated from a Butane Diacetal Desymmetrized Glycolic Acid Derivative We gratefully acknowledge financial support from the EPSRC (to D.J.D.), the EU (Marie Curie Fellowship to F.R.), and the Novartis Research Fellowship (to S.V.L.). We are also indebted to Dr. John E. Davis for the X-ray crystal structure determinations.
gan: Dixon, D, et al.
Cyhoeddwyd: (2001)

Understanding the origins of remote asymmetric induction in the boron aldol reactions of beta-alkoxy methyl ketones.
gan: Paton, R, et al.
Cyhoeddwyd: (2006)

NHC-catalyzed regiodivergent transformations of Ynones with trifluoromethyl ketones: Aldol reaction or [3+2] annulation
gan: Fangfang Lu, et al.
Cyhoeddwyd: (2023-08-01)

Asymmetric cross-aldol reaction of isatin and ketones catalyzed by crude earthworm extract as efficient biocatalyst
gan: Fatemeh Shams, et al.
Cyhoeddwyd: (2020-07-01)

Diastereoselective intramolecular aldol ring closures of threonine derivatives leading to densely functionalised pyroglutamates related to oxazolomycin
gan: Heaviside, E, et al.
Cyhoeddwyd: (2014)

Hypervalent Iodine-Mediated Diastereoselective α-Acetoxylation of Cyclic Ketones
gan: Jiashen Tan, et al.
Cyhoeddwyd: (2020-07-01)

Enantio- and diastereoselective catalytic alkylation reactions with aziridines.
gan: Moss, T, et al.
Cyhoeddwyd: (2008)

Modern aldol reactions /
gan: Mahrwald, Rainer
Cyhoeddwyd: (2004)

Enantioselective desymmetrisation of an epoxytropinone for peduncularine synthesis
gan: Shelton, RE, et al.
Cyhoeddwyd: (2020)