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The Chelation-controlled Mukaiyama Aldol Reaction of Chiral α- and β-Alkoxy Aldehydes

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Roiban,  Georghe-Doru
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Philipps-Universität Marburg, Fachbereich Chemie;

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Ilie,  Adriana
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Philipps-Universität Marburg, Fachbereich Chemie;

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Reetz,  Manfred T.
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Philipps-Universität Marburg, Fachbereich Chemie;

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Citation

Roiban, G.-D., Ilie, A., & Reetz, M. T. (2014). The Chelation-controlled Mukaiyama Aldol Reaction of Chiral α- and β-Alkoxy Aldehydes. Chemistry Letters, 43 (2014)(1), 2-10. doi:10.1246/cl.130920.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0024-557D-A
Abstract
The concept of treating chiral α- and β-alkoxy aldehydes with bicoordinate Lewis acids such as TiCl4, SnCl4, or MgBr2 followed by the addition of carbon nucleophiles for achieving chelation control with 1,2- and 1,3-asymmetric induction, respectively, was introduced three decades ago and has since evolved into a general method. In the case of enol silanes, the chelation-controlled Mukaiyama aldol reaction is involved, which has been used in recent natural products syntheses.