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Domino-hydroformylation/aldol condensation catalysis: highly selective synthesis of α,β-unsaturated aldehydes from olefins.
Chemistry. 2014 Oct 06; 20(41):13210-6.C

Abstract

A general and highly chemo-, regio-, and stereoselective synthesis of α,β-unsaturated aldehydes by a domino hydroformylation/aldol condensation reaction has been developed. A variety of olefins and aromatic aldehydes were efficiently converted into various substituted α,β-unsaturated aldehydes in good to excellent yields in the presence of a rhodium phosphine/acid-base catalyst system. In view of the easy availability of the substrates, the high atom-efficiency, the excellent selectivity, and the mild conditions, this method is expected to complement current methodologies for the preparation of α,β-unsaturated aldehydes.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Fang X
Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany).
Jackstell R
No affiliation info available
Franke R
No affiliation info available
Beller M
No affiliation info available

MeSH

AldehydesAlkenesCatalysisPhosphinesRhodiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

25179918

Citation

Fang, Xianjie, et al. "Domino-hydroformylation/aldol Condensation Catalysis: Highly Selective Synthesis of Α,β-unsaturated Aldehydes From Olefins." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 20, no. 41, 2014, pp. 13210-6.
Fang X, Jackstell R, Franke R, et al. Domino-hydroformylation/aldol condensation catalysis: highly selective synthesis of α,β-unsaturated aldehydes from olefins. Chemistry. 2014;20(41):13210-6.
Fang, X., Jackstell, R., Franke, R., & Beller, M. (2014). Domino-hydroformylation/aldol condensation catalysis: highly selective synthesis of α,β-unsaturated aldehydes from olefins. Chemistry (Weinheim an Der Bergstrasse, Germany), 20(41), 13210-6. https://doi.org/10.1002/chem.201403302
Fang X, et al. Domino-hydroformylation/aldol Condensation Catalysis: Highly Selective Synthesis of Α,β-unsaturated Aldehydes From Olefins. Chemistry. 2014 Oct 6;20(41):13210-6. PubMed PMID: 25179918.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Domino-hydroformylation/aldol condensation catalysis: highly selective synthesis of α,β-unsaturated aldehydes from olefins. AU - Fang,Xianjie, AU - Jackstell,Ralf, AU - Franke,Robert, AU - Beller,Matthias, Y1 - 2014/09/01/ PY - 2014/04/29/received PY - 2014/9/3/entrez PY - 2014/9/3/pubmed PY - 2015/6/3/medline KW - catalysis KW - domino reactions KW - hydroformylation KW - olefins KW - unsaturated aldehydes SP - 13210 EP - 6 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 20 IS - 41 N2 - A general and highly chemo-, regio-, and stereoselective synthesis of α,β-unsaturated aldehydes by a domino hydroformylation/aldol condensation reaction has been developed. A variety of olefins and aromatic aldehydes were efficiently converted into various substituted α,β-unsaturated aldehydes in good to excellent yields in the presence of a rhodium phosphine/acid-base catalyst system. In view of the easy availability of the substrates, the high atom-efficiency, the excellent selectivity, and the mild conditions, this method is expected to complement current methodologies for the preparation of α,β-unsaturated aldehydes. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/25179918/Domino_hydroformylation/aldol_condensation_catalysis:_highly_selective_synthesis_of_αβ_unsaturated_aldehydes_from_olefins_ DB - PRIME DP - Unbound Medicine ER -