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Catalytic enantioselective domino oxa-michael/aldol condensations: asymmetric synthesis of benzopyran derivatives.
Chemistry. 2007; 13(2):574-81.C

Abstract

The first direct organocatalytic asymmetric domino oxa-Michael/aldol condensation reaction is presented. The unprecedentedly simple, chiral, pyrrolidine-catalyzed asymmetric domino reactions between salicylic aldehyde derivatives and alpha,beta-unsaturated aldehydes proceed with high chemo- and enantioselectivities to give the corresponding chromene-3-carbaldehyde derivatives in high yields and with ee values of 83-98%.

Authors+Show Affiliations

Sundén H
Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden.
Ibrahem I
No affiliation info available
Zhao GL
No affiliation info available
Eriksson L
No affiliation info available
Córdova A
No affiliation info available

MeSH

AldehydesBenzaldehydesBenzopyransCatalysisCrystallography, X-RayCyclizationHeterocyclic CompoundsModels, MolecularMolecular ConformationMolecular StructureSolventsStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17039558

Citation

Sundén, Henrik, et al. "Catalytic Enantioselective Domino Oxa-michael/aldol Condensations: Asymmetric Synthesis of Benzopyran Derivatives." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 13, no. 2, 2007, pp. 574-81.
Sundén H, Ibrahem I, Zhao GL, et al. Catalytic enantioselective domino oxa-michael/aldol condensations: asymmetric synthesis of benzopyran derivatives. Chemistry. 2007;13(2):574-81.
Sundén, H., Ibrahem, I., Zhao, G. L., Eriksson, L., & Córdova, A. (2007). Catalytic enantioselective domino oxa-michael/aldol condensations: asymmetric synthesis of benzopyran derivatives. Chemistry (Weinheim an Der Bergstrasse, Germany), 13(2), 574-81.
Sundén H, et al. Catalytic Enantioselective Domino Oxa-michael/aldol Condensations: Asymmetric Synthesis of Benzopyran Derivatives. Chemistry. 2007;13(2):574-81. PubMed PMID: 17039558.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic enantioselective domino oxa-michael/aldol condensations: asymmetric synthesis of benzopyran derivatives. AU - Sundén,Henrik, AU - Ibrahem,Ismail, AU - Zhao,Gui-Ling, AU - Eriksson,Lars, AU - Córdova,Armando, PY - 2006/10/14/pubmed PY - 2007/3/27/medline PY - 2006/10/14/entrez SP - 574 EP - 81 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 13 IS - 2 N2 - The first direct organocatalytic asymmetric domino oxa-Michael/aldol condensation reaction is presented. The unprecedentedly simple, chiral, pyrrolidine-catalyzed asymmetric domino reactions between salicylic aldehyde derivatives and alpha,beta-unsaturated aldehydes proceed with high chemo- and enantioselectivities to give the corresponding chromene-3-carbaldehyde derivatives in high yields and with ee values of 83-98%. SN - 0947-6539 UR - https://www.unboundmedicine.com/medline/citation/17039558/Catalytic_enantioselective_domino_oxa_michael/aldol_condensations:_asymmetric_synthesis_of_benzopyran_derivatives_ L2 - https://doi.org/10.1002/chem.200600572 DB - PRIME DP - Unbound Medicine ER -