José M. Odriozola
Universidad Pública de Navarra
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Featured researches published by José M. Odriozola.
Chemical Science | 2013
Enrique Gómez-Bengoa; Jesús García; Sandra Jiménez; Irati Lapuerta; Antonia Mielgo; José M. Odriozola; Itziar Otazo; Jesús Razkin; Iñaki Urruzuno; Silvia Vera; Mikel Oiarbide; Claudio Palomo
A catalytic and highly stereoselective entry to propargylic alcohols and products derived thereof is reported based on an unprecedented cross-aldol coupling between unmodified aldehydes and ynals. The method requires an amine–metal salt–Bronsted acid ternary catalyst system and implies synergistic activation of the donor aldehyde via enamine and of the acceptor carbonyl via unique and reversible metal–alkyne complexation. Specifically, by using a combined a,a-dialkylprolinol silyl ether–CuI–PhCO2H catalyst system, remarkably high levels of diastereo- and enantioselectivity (anti/syn up to >20 : 1, ee up to >99%) are achieved.
Journal of The Chemical Society, Chemical Communications | 1988
José M. Odriozola; Fernando P. Cossío; Claudio Palomo
A practical stereoselective synthesis of 4-acetoxy-3-ethylazetidin-2-one via Reformatsky reaction between methyl-α-bromobutyrate and N-4-methoxyphenyl-α-methylcinnamyildeneamine is described.
Tetrahedron-asymmetry | 1999
José M. Odriozola; Jesús García; Alberto González; Pilar Gil
Abstract Syntheses of phoenicol, ferrugineol, and cruentol, aggregation pheromones of Rhynchophorus palm weevils, have been achieved with an overall yield of 42, 40 and 41%, respectively (five steps), in high enantiomeric purity.
Journal of The Chemical Society, Chemical Communications | 1995
Claudio Palomo; José I. Miranda; Carmen Cuevas; José M. Odriozola
A new route to natural products containing 1,2-diol and 1,2-amino alcohol subunits based on the [2 + 2] cycloaddition of dichloroketene to α-oxyaldehydes and α-amino aldehydes is demonstrated.
Tetrahedron-asymmetry | 2003
Elena Arceo; José M. Odriozola; Jesús García; Alberto González; Pilar Gil
Synthesis of (R)-4-hexanolide, a sexual pheromone of Trogoderma glabrum, has been achieved with an overall yield of 45.4% in high enantiomeric purity using a chiral auxiliary derived from (S)-camphor.
Chemistry: A European Journal | 2016
Igor Iriarte; Silvia Vera; Eider Badiola; Antonia Mielgo; Mikel Oiarbide; Jesús García; José M. Odriozola; Claudio Palomo
An efficient, highly diastereo- and enantioselective assembly of acyclic carbonyl fragments possessing nonadjacent all-carbon tertiary/quaternary stereoarrays is reported based on a Brønsted base catalyzed Michael addition/α-protonation sequence involving α-cyanoacetates and 2,4-dimethyl-4-hydroxypenten-3-one as novel methacrylate equivalent.
Journal of The Chemical Society, Chemical Communications | 1989
Fernando P. Cossío; José M. Odriozola; Mikel Oiarbide; Claudio Palomo
Ethyl bromoacetate reacts with imines in the presence of zinc activated by trimethylchlorosilane to give high yields of 3-unsubstituted β-lactams.
Journal of The Chemical Society, Chemical Communications | 1990
Claudio Palomo; Jesus M. Ontoria; José M. Odriozola; Jesús M. Alzpurua; Iñtaki Ganboa
The dehydrochlorination of alkanoyl chlorides with triethylamine in the presence of α-iminoesters produced 3-alkyl-4-alkoxycarbonyl β-lactams in excellent yields and high stereoselectivity.
Chemistry: A European Journal | 2014
Jesús García; José M. Odriozola; Jesús Razkin; Irati Lapuerta; Amaiur Odriozola; Iñaki Urruzuno; Silvia Vera; Mikel Oiarbide; Claudio Palomo
An effective asymmetric route to functionalized 1,6- and 1,7-enynes has been developed based on a direct cross-aldol reaction between ω-unsaturated aldehydes and propargylic aldehydes (α,β-ynals) promoted by combined α,α-dialkylprolinol ether/Brønsted acid catalysis. This synergistic activation strategy is key to accessing the corresponding aldol adducts with high stereoselectivity, both enantio- and diastereoselectivity. The aldol reaction also proceeds well with propargylic ketones (α,β-ynones) thus enabling a stereocontrolled access to the corresponding tertiary alcohols. The utility of these adducts, which are difficult to prepare through standard methodology, is demonstrated by their transformation into trisubstituted bicyclic enones using standard Pauson-Khand conditions.
Chemistry: A European Journal | 2018
Iurre Olaizola; Teresa E. Campano; Igor Iriarte; Silvia Vera; Antonia Mielgo; Jesús García; José M. Odriozola; Mikel Oiarbide; Claudio Palomo
The catalyst-controlled enantioselective direct addition reaction of enolizable esters and related carboxylic acid derivatives to π electrophiles remains a difficult synthetic transformation. In this study, the suitability of α-hydroxy ketones as ester equivalents capable of being activated by bifunctional Brønsted base catalysts in the context of conjugate addition reactions to nitroolefins is demonstrated. The scope of the reaction, which affords the corresponding Michael adducts with very high stereoselectivity (diastereomeric ratio (d.r.) ≥95:5, up to 99 % enantiomeric excess (ee)), and its limitations are explored, as is the aftermath elaboration of adducts into densely functionalized enantioenriched products.