A5007265733- Asymmetric Synthesis and Catalysis
- Synthetic Organic Chemistry Methods
- Asymmetric Hydrogenation and Catalysis
- Chemical Synthesis and Analysis
- Synthesis and Catalytic Reactions
- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Chemical Synthesis and Reactions
- Carbohydrate Chemistry and Synthesis
- Oxidative Organic Chemistry Reactions
- Catalytic C–H Functionalization Methods
- Advanced Synthetic Organic Chemistry
- Microbial Natural Products and Biosynthesis
- Click Chemistry and Applications
- Marine Sponges and Natural Products
- Cyclopropane Reaction Mechanisms
- Chemical synthesis and alkaloids
- Analytical Chemistry and Chromatography
- Sulfur-Based Synthesis Techniques
- Coordination Chemistry and Organometallics
- Glycosylation and Glycoproteins Research
- Synthesis and Reactivity of Sulfur-Containing Compounds
- Inorganic and Organometallic Chemistry
- Chemical Reactions and Isotopes
- Enzyme Catalysis and Immobilization
Universitat de Barcelona
2015-2024
Institut de Biomedicina de la Universitat de Barcelona
2014-2023
Instituto de Química Orgánica General
2016-2018
FC Barcelona
2016-2018
Institute for Biomedicine
2017-2018
Thieme Medical Publishers (Germany)
2011
Instituto de Investigaciones Químicas y Ambientales de Barcelona
2003-2008
Consejo Superior de Investigaciones Científicas
2008
University of Cambridge
1994-1995
Chemo (Spain)
1993
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTStudies in Macrolide Synthesis: A Stereocontrolled Synthesis of Oleandolide Employing Reagent- and Substrate-Controlled Aldol Reactions (S)-1-(Benzyloxy)-2-methylpentan-3-oneIan Paterson, Roger D. Norcross, Richard A. Ward, Pedro Romea, M. Anne ListerCite this: J. Am. Chem. Soc. 1994, 116, 25, 11287–11314Publication Date (Print):December 1, 1994Publication History Published online1 May 2002Published inissue 1 December...
Morpholine-derived amides react with RMgX to give the corresponding ketones in good yield. The mild conditions required and low cost of starting materials make this method very appealing for large scale preparations.
A direct and asymmetric syn-aldol reaction of N-acyl-1,3-oxazinane-2-thiones with dialkyl acetals from aromatic in the presence 2-5 mol % [DTBM-SEGPHOS]NiCl2, TMSOTf, lutidine has been developed. It established that oxazinanethione heterocycle, used for first time as a scaffold carbon-carbon bond-forming reactions, can be smoothly removed to give access variety enantiomerically pure compounds high synthetic value.
[reaction: see text] High stereoselectivities (up to 98% de) have been achieved for the Lewis acid-mediated cross-coupling reaction of dimethyl acetals a chiral 1,3-thiazolidine-2-thione-derived titanium enolate. The affords enantiopure anti alpha-methyl-beta-alkoxy carbonyl compounds in wide range acetals.
Experimental and theoretical studies evidence an unconventional biradical character for the titanium enolates derived from α-alkoxy ketones TiCl4. EPR experiments ab initio calculations suggest that these have open shell electronic ground state.
A substrate-controlled synthesis of (+)-herboxidiene from two lactate-derived chiral ketones is described. Remarkably, most the carbon backbone was constructed through highly stereoselective titanium-mediated aldol reactions and an Ireland–Claisen rearrangement. Furthermore, oxa-Michael cyclization a high-yield Suzuki coupling were used to assemble pyran ring diene moiety respectively.
Alternative titanium-mediated aldol procedures based on several protected β-hydroxy ethyl ketones have been surveyed. Eventually, enolization of (S)-1-benzyloxy-2-methyl-3-pentanone (1) with (i-PrO)TiCl3/i-Pr2NEt provided a very reactive enolate that afforded the corresponding 2,4-syn-4,5-syn adducts in high yields and diastereomeric ratios broad range aldehydes
Abstract A direct and asymmetric aldol reaction of N ‐acyl thiazinanethiones with aromatic aldehydes catalyzed by chiral nickel(II) complexes is reported. The gives the corresponding O ‐TIPS‐protected anti ‐aldol adducts in high yields remarkable stereocontrol atom economy. Furthermore, straightforward removal achiral scaffold provides enantiomerically pure intermediates synthetic interest, which involve precursors for ‐α‐amino‐β‐hydroxy α,β‐dihydroxy carboxylic derivatives. Theoretical...
[reaction: see text] Highly stereoselective titanium-mediated aldol reactions based on lactate-derived ketones are reported. The stereochemical outcome of the process depends protecting group (PMB or Bn) and Lewis acid (i-PrOTiCl(3) TiCl(4)) used in enolization step, corresponding anti-syn syn-syn aldols being prepared high yields with diastereomeric ratios up to 99:1.
Abstract A highly efficient and straightforward aminoxylation of titanium(IV) enolates from ( S )‐ N ‐acyl‐4‐benzyl‐5,5‐dimethyl‐1,3‐oxazolidin‐2‐ones with TEMPO has been developed. wide array functional groups on the acyl moiety, including alkyl aryl substituents, olefins, esters, or α‐cyclopropyl, as well α‐trifluoromethyl groups, are tolerated. This transformation can therefore produce α‐aminoxylated adducts in excellent yields high diastereomeric ratios (d.r.). In turn, parallel...
A convergent and module-based strategy for the asymmetric synthesis of western hemisphere (C1−C17 fragment) salinomycin has been devised. This new synthetic approach relies on highly stereoselective C-glycosidation aldol processes.
Highly diastereoselective (i-PrO)2TiCl2-mediated aldol reactions from lactate-derived α′-halo α-silyloxy ketones and subsequent treatment of the resultant aldols with a wide range nucleophiles furnishes highly functionalized arrangements useful in natural product syntheses.
Lewis acid mediated addition of chiral titanium enolates to glycals provides either α- or β-1'-methyl-substituted C-glycosides. This highly stereoselective methodology permits the modular preparation three four possible diastereomers.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTImproved methods for the N-nitration of amidesPedro Romea, Montse Aragones, Jordi Garcia, and Jaume VilarrasaCite this: J. Org. Chem. 1991, 56, 25, 7038–7042Publication Date (Print):December 1, 1991Publication History Published online1 May 2002Published inissue 1 December 1991https://pubs.acs.org/doi/10.1021/jo00025a017https://doi.org/10.1021/jo00025a017research-articleACS PublicationsRequest reuse permissionsArticle...
The Lewis acid-mediated addition of titanium enolates from 1 to dimethyl ketals aliphatic methyl ketones followed by removal the chiral auxiliary furnishes enantiomerically pure derivatives containing a tertiary ether and contiguous stereocenter in straightforward manner.
Substrate-controlled titanium-mediated aldol reactions from (S)-4-benzyloxy-3-methyl-2-butanone provide satisfactory levels of 2,5-syn asymmetric induction if they are carried out in the presence a second equivalent TiCl4. Such give high yields and excellent diastereoselectivity with wide array achiral chiral aldehydes without needing other sources chirality. This procedure is thus interest for synthesis natural products. Furthermore, spectroscopic studies analyses reacting species have...