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Asymmetric vinylogous Mukaiyama aldol reaction of aldehyde-derived dienolates.
Org Lett. 2011 May 06; 13(9):2430-2.OL

Abstract

Unsaturated aldehydes are exquisite building blocks for further transformations in polyketide synthesis. Besides standard transformations that take advantage of the aldehyde functionality, the conjugate addition of hydrides followed by internal protonation allows access to alpha chiral aldehydes. Even though vinylogous Mukaiyama aldol reactions have been used in natural product syntheses before, the first enantioselective Mukaiyama aldol reaction of aldehyde-derived dienolates is described.

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Authors+Show Affiliations

Gieseler MT
Institut für Organische Chemie, Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover, Germany.
Kalesse M
No affiliation info available

MeSH

AldehydesAnionsMolecular StructureProtonsStereoisomerismVinyl Compounds

Pub Type(s)

Journal Article

Language

eng

PubMed ID

21473644

Citation

Gieseler, Marc T., and Markus Kalesse. "Asymmetric Vinylogous Mukaiyama Aldol Reaction of Aldehyde-derived Dienolates." Organic Letters, vol. 13, no. 9, 2011, pp. 2430-2.
Gieseler MT, Kalesse M. Asymmetric vinylogous Mukaiyama aldol reaction of aldehyde-derived dienolates. Org Lett. 2011;13(9):2430-2.
Gieseler, M. T., & Kalesse, M. (2011). Asymmetric vinylogous Mukaiyama aldol reaction of aldehyde-derived dienolates. Organic Letters, 13(9), 2430-2. https://doi.org/10.1021/ol2006727
Gieseler MT, Kalesse M. Asymmetric Vinylogous Mukaiyama Aldol Reaction of Aldehyde-derived Dienolates. Org Lett. 2011 May 6;13(9):2430-2. PubMed PMID: 21473644.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric vinylogous Mukaiyama aldol reaction of aldehyde-derived dienolates. AU - Gieseler,Marc T, AU - Kalesse,Markus, Y1 - 2011/04/07/ PY - 2011/4/9/entrez PY - 2011/4/9/pubmed PY - 2011/7/30/medline SP - 2430 EP - 2 JF - Organic letters JO - Org Lett VL - 13 IS - 9 N2 - Unsaturated aldehydes are exquisite building blocks for further transformations in polyketide synthesis. Besides standard transformations that take advantage of the aldehyde functionality, the conjugate addition of hydrides followed by internal protonation allows access to alpha chiral aldehydes. Even though vinylogous Mukaiyama aldol reactions have been used in natural product syntheses before, the first enantioselective Mukaiyama aldol reaction of aldehyde-derived dienolates is described. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/21473644/Asymmetric_vinylogous_Mukaiyama_aldol_reaction_of_aldehyde_derived_dienolates_ L2 - https://doi.org/10.1021/ol2006727 DB - PRIME DP - Unbound Medicine ER -