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Synfacts 2010(7): 0788-0788
DOI: 10.1055/s-0029-1220035
DOI: 10.1055/s-0029-1220035
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
MgI2-Accelerated Enantioselective ;Morita-Baylis-Hillman Reactions
A. Bugarin, B. T. Connell*
Texas A&M University, College Station, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. Juni 2010 (online)
Significance
The Morita-Baylis-Hillman reaction is an atom-economical method of rapid increase of molecular complexity. The development of asymmetric modifications of this process has received considerable attention in recent years. In this paper the authors developed a highly enantio-selective system based on Fu’s planar chiral DMAP derivative 1. It was shown that the applicability of the reaction can be expanded by the use of a simple Lewis acid co-catalyst (50 mol% MgI2). The protocol appeared to be most efficient for aromatic aldehydes. Enantioselectivities of up to 98% ee were obtained accompanied by good to excellent yields. Aliphatic substrates demonstrated inferior results.