A single-step synthesis of 4-oxazolin-2-ones and their use in the construction of polycyclic structures bearing quaternary stereocenters

Blanca M. Santoyo; Carlos González-Romero; Omar Merino; Rafael Martínez-Palou; Aydeé Fuentes-Benites; Hugo A. Jiménez-Vázquez; Francisco Delgado; Joaquín Tamariz

doi:10.1002/ejoc.200900114

A single-step synthesis of 4-oxazolin-2-ones and their use in the construction of polycyclic structures bearing quaternary stereocenters

Blanca M. Santoyo, Carlos González-Romero, Omar Merino, Rafael Martínez-Palou, Aydeé Fuentes-Benites, Hugo A. Jiménez-Vázquez, Francisco Delgado, Joaquín Tamariz

Escuela Nacional de Ciencias Biológicas (ENCB)

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

Abstract

A new method for the synthesis of 4-oxazolin-2-ones by a one-pot MW-promoted condensation of a-ketols and isocyanates is reported. An alternative thermal approach using the same starting materials is also described. These cyclic enamides were efficient nucleophiles, reacting with Michael acceptors and prenyl bromide to give a variety of polycyclic structures bearing one or two quaternary stereocenters. The selectivity of the products depended on the reaction conditions and on the electrophile used.

Original language	English
Pages (from-to)	2505-2518
Number of pages	14
Journal	European Journal of Organic Chemistry
Issue number	15
DOIs	https://doi.org/10.1002/ejoc.200900114
State	Published - May 2009

Keywords

Domino reactions
Heterocycles
Michael addition
Microwaves reactions
Quaternary stereocenters

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10.1002/ejoc.200900114

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Santoyo, B. M., González-Romero, C., Merino, O., Martínez-Palou, R., Fuentes-Benites, A., Jiménez-Vázquez, H. A., Delgado, F., & Tamariz, J. (2009). A single-step synthesis of 4-oxazolin-2-ones and their use in the construction of polycyclic structures bearing quaternary stereocenters. European Journal of Organic Chemistry, (15), 2505-2518. https://doi.org/10.1002/ejoc.200900114

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title = "A single-step synthesis of 4-oxazolin-2-ones and their use in the construction of polycyclic structures bearing quaternary stereocenters",

abstract = "A new method for the synthesis of 4-oxazolin-2-ones by a one-pot MW-promoted condensation of a-ketols and isocyanates is reported. An alternative thermal approach using the same starting materials is also described. These cyclic enamides were efficient nucleophiles, reacting with Michael acceptors and prenyl bromide to give a variety of polycyclic structures bearing one or two quaternary stereocenters. The selectivity of the products depended on the reaction conditions and on the electrophile used.",

keywords = "Domino reactions, Heterocycles, Michael addition, Microwaves reactions, Quaternary stereocenters",

author = "Santoyo, {Blanca M.} and Carlos Gonz{\'a}lez-Romero and Omar Merino and Rafael Mart{\'i}nez-Palou and Ayde{\'e} Fuentes-Benites and Jim{\'e}nez-V{\'a}zquez, {Hugo A.} and Francisco Delgado and Joaqu{\'i}n Tamariz",

year = "2009",

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Santoyo, BM, González-Romero, C, Merino, O, Martínez-Palou, R, Fuentes-Benites, A, Jiménez-Vázquez, HA , Delgado, F & Tamariz, J 2009, 'A single-step synthesis of 4-oxazolin-2-ones and their use in the construction of polycyclic structures bearing quaternary stereocenters', European Journal of Organic Chemistry, no. 15, pp. 2505-2518. https://doi.org/10.1002/ejoc.200900114

TY - JOUR

T1 - A single-step synthesis of 4-oxazolin-2-ones and their use in the construction of polycyclic structures bearing quaternary stereocenters

AU - Santoyo, Blanca M.

AU - González-Romero, Carlos

AU - Merino, Omar

AU - Martínez-Palou, Rafael

AU - Fuentes-Benites, Aydeé

AU - Jiménez-Vázquez, Hugo A.

AU - Delgado, Francisco

AU - Tamariz, Joaquín

PY - 2009/5

Y1 - 2009/5

N2 - A new method for the synthesis of 4-oxazolin-2-ones by a one-pot MW-promoted condensation of a-ketols and isocyanates is reported. An alternative thermal approach using the same starting materials is also described. These cyclic enamides were efficient nucleophiles, reacting with Michael acceptors and prenyl bromide to give a variety of polycyclic structures bearing one or two quaternary stereocenters. The selectivity of the products depended on the reaction conditions and on the electrophile used.

AB - A new method for the synthesis of 4-oxazolin-2-ones by a one-pot MW-promoted condensation of a-ketols and isocyanates is reported. An alternative thermal approach using the same starting materials is also described. These cyclic enamides were efficient nucleophiles, reacting with Michael acceptors and prenyl bromide to give a variety of polycyclic structures bearing one or two quaternary stereocenters. The selectivity of the products depended on the reaction conditions and on the electrophile used.

KW - Domino reactions

KW - Heterocycles

KW - Michael addition

KW - Microwaves reactions

KW - Quaternary stereocenters

UR - http://www.scopus.com/inward/record.url?scp=66149158535&partnerID=8YFLogxK

U2 - 10.1002/ejoc.200900114

DO - 10.1002/ejoc.200900114

M3 - Artículo

SN - 1434-193X

SP - 2505

EP - 2518

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 15

ER -

A single-step synthesis of 4-oxazolin-2-ones and their use in the construction of polycyclic structures bearing quaternary stereocenters

Abstract

Keywords

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