Enantioselective aldol reactions with aqueous 2,2-dimethoxyacetaldehyde organocatalyzed by binam-prolinamides under solvent-free conditions
Aqueous 2,2-dimethoxyacetaldehyde (60% wt solution) is used as an acceptor in aldol reactions, with cyclic and acyclic ketones and aldehydes as donors, organocatalyzed by 10 mol % of N-tosyl-(Sa)-binam-l-prolinamide [(Sa)-binam-sulfo-l-Pro] at rt under solvent-free conditions. The corresponding mono...
Published in: | Tetrahedron: Asymmetry |
---|---|
Main Authors: | , , , |
Other Authors: | , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
Elsevier
2014
|
Subjects: | |
Online Access: | http://hdl.handle.net/10045/40921 https://doi.org/10.1016/j.tetasy.2014.08.012 |
id |
ftunivalicante:oai:rua.ua.es:10045/40921 |
---|---|
record_format |
openpolar |
spelling |
ftunivalicante:oai:rua.ua.es:10045/40921 2023-05-15T17:53:48+02:00 Enantioselective aldol reactions with aqueous 2,2-dimethoxyacetaldehyde organocatalyzed by binam-prolinamides under solvent-free conditions Navarro Moles, Fernando Javier Bañón Caballero, Abraham Guillena, Gabriela Nájera, Carmen Universidad de Alicante. Departamento de Química Orgánica Universidad de Alicante. Instituto Universitario de Síntesis Orgánica Síntesis Asimétrica (SINTAS) 2014-10-15 http://hdl.handle.net/10045/40921 https://doi.org/10.1016/j.tetasy.2014.08.012 eng eng Elsevier http://dx.doi.org/10.1016/j.tetasy.2014.08.012 Tetrahedron: Asymmetry. 2014, 25(18-19): 1323-1330. doi:10.1016/j.tetasy.2014.08.012 0957-4166 (Print) 1362-511X (Online) http://hdl.handle.net/10045/40921 doi:10.1016/j.tetasy.2014.08.012 A7448367 info:eu-repo/semantics/openAccess Enantioselective Aldol Aqueous Solvent free Prolinamides Química Orgánica info:eu-repo/semantics/article 2014 ftunivalicante https://doi.org/10.1016/j.tetasy.2014.08.012 2020-06-05T13:09:00Z Aqueous 2,2-dimethoxyacetaldehyde (60% wt solution) is used as an acceptor in aldol reactions, with cyclic and acyclic ketones and aldehydes as donors, organocatalyzed by 10 mol % of N-tosyl-(Sa)-binam-l-prolinamide [(Sa)-binam-sulfo-l-Pro] at rt under solvent-free conditions. The corresponding monoprotected 2-hydroxy-1,4-dicarbonyl compounds are obtained in good yields and with high levels of diastereo- and enantioselectivity mainly as anti-aldols. In the case of 4-substituted cyclohexanones a desymmetrization process takes place to mainly afford the anti,anti-aldols. 2,2-Dimethyl-1,3-dioxan-5-one allows the synthesis of a useful intermediate for the preparation of carbohydrates in higher yield, de and ee than with l-Pro as the organocatalyst. We thank the financial support from the Spanish Ministerio de Economía y Competitividad (MINECO, Projects CTQ2010-20387 and Consolider Ingenio 2010, CSD2007-00006), FEDER, the Generalitat Valenciana (Prometeo/2009/039), the University of Alicante and the European Commission (ORCA action CM0905). A.B.-C. thanks Spanish MINECO for a predoctoral fellowship (FPU AP2009-3601). Article in Journal/Newspaper Orca RUA - Repositorio Institucional de la Universidad de Alicante Tetrahedron: Asymmetry 25 18-19 1323 1330 |
institution |
Open Polar |
collection |
RUA - Repositorio Institucional de la Universidad de Alicante |
op_collection_id |
ftunivalicante |
language |
English |
topic |
Enantioselective Aldol Aqueous Solvent free Prolinamides Química Orgánica |
spellingShingle |
Enantioselective Aldol Aqueous Solvent free Prolinamides Química Orgánica Navarro Moles, Fernando Javier Bañón Caballero, Abraham Guillena, Gabriela Nájera, Carmen Enantioselective aldol reactions with aqueous 2,2-dimethoxyacetaldehyde organocatalyzed by binam-prolinamides under solvent-free conditions |
topic_facet |
Enantioselective Aldol Aqueous Solvent free Prolinamides Química Orgánica |
description |
Aqueous 2,2-dimethoxyacetaldehyde (60% wt solution) is used as an acceptor in aldol reactions, with cyclic and acyclic ketones and aldehydes as donors, organocatalyzed by 10 mol % of N-tosyl-(Sa)-binam-l-prolinamide [(Sa)-binam-sulfo-l-Pro] at rt under solvent-free conditions. The corresponding monoprotected 2-hydroxy-1,4-dicarbonyl compounds are obtained in good yields and with high levels of diastereo- and enantioselectivity mainly as anti-aldols. In the case of 4-substituted cyclohexanones a desymmetrization process takes place to mainly afford the anti,anti-aldols. 2,2-Dimethyl-1,3-dioxan-5-one allows the synthesis of a useful intermediate for the preparation of carbohydrates in higher yield, de and ee than with l-Pro as the organocatalyst. We thank the financial support from the Spanish Ministerio de Economía y Competitividad (MINECO, Projects CTQ2010-20387 and Consolider Ingenio 2010, CSD2007-00006), FEDER, the Generalitat Valenciana (Prometeo/2009/039), the University of Alicante and the European Commission (ORCA action CM0905). A.B.-C. thanks Spanish MINECO for a predoctoral fellowship (FPU AP2009-3601). |
author2 |
Universidad de Alicante. Departamento de Química Orgánica Universidad de Alicante. Instituto Universitario de Síntesis Orgánica Síntesis Asimétrica (SINTAS) |
format |
Article in Journal/Newspaper |
author |
Navarro Moles, Fernando Javier Bañón Caballero, Abraham Guillena, Gabriela Nájera, Carmen |
author_facet |
Navarro Moles, Fernando Javier Bañón Caballero, Abraham Guillena, Gabriela Nájera, Carmen |
author_sort |
Navarro Moles, Fernando Javier |
title |
Enantioselective aldol reactions with aqueous 2,2-dimethoxyacetaldehyde organocatalyzed by binam-prolinamides under solvent-free conditions |
title_short |
Enantioselective aldol reactions with aqueous 2,2-dimethoxyacetaldehyde organocatalyzed by binam-prolinamides under solvent-free conditions |
title_full |
Enantioselective aldol reactions with aqueous 2,2-dimethoxyacetaldehyde organocatalyzed by binam-prolinamides under solvent-free conditions |
title_fullStr |
Enantioselective aldol reactions with aqueous 2,2-dimethoxyacetaldehyde organocatalyzed by binam-prolinamides under solvent-free conditions |
title_full_unstemmed |
Enantioselective aldol reactions with aqueous 2,2-dimethoxyacetaldehyde organocatalyzed by binam-prolinamides under solvent-free conditions |
title_sort |
enantioselective aldol reactions with aqueous 2,2-dimethoxyacetaldehyde organocatalyzed by binam-prolinamides under solvent-free conditions |
publisher |
Elsevier |
publishDate |
2014 |
url |
http://hdl.handle.net/10045/40921 https://doi.org/10.1016/j.tetasy.2014.08.012 |
genre |
Orca |
genre_facet |
Orca |
op_relation |
http://dx.doi.org/10.1016/j.tetasy.2014.08.012 Tetrahedron: Asymmetry. 2014, 25(18-19): 1323-1330. doi:10.1016/j.tetasy.2014.08.012 0957-4166 (Print) 1362-511X (Online) http://hdl.handle.net/10045/40921 doi:10.1016/j.tetasy.2014.08.012 A7448367 |
op_rights |
info:eu-repo/semantics/openAccess |
op_doi |
https://doi.org/10.1016/j.tetasy.2014.08.012 |
container_title |
Tetrahedron: Asymmetry |
container_volume |
25 |
container_issue |
18-19 |
container_start_page |
1323 |
op_container_end_page |
1330 |
_version_ |
1766161505436303360 |