Stereoselective Reductive Condensation Reactions

University Of North Carolina Chapel Hill, Chapel Hill NC

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Abstract

DESCRIPTION (provided by applicant): In this proposal, a program directed towards the development of novel and synthetically valuable stereoselective catalytic reductive condensations reactions is described. In our initial studies we have developed the catalytic enantioselective reductive aldol reaction which converts commercially available silanes, acrylates and aldehydes to aldol adducts. The reductive aldol reaction holds an advantage over auxiliary-based and Mukaiyama aldol processes in that the reductive aldol reaction directly provides silyl protected aldol adducts, proceeds at room temperature and operates directly on commercially available materials. In the proposed research, we aim to develop related processes that have similar operational simplicity but which afford reaction products which are not readily available by current catalytic asymmetric processes. Since non-oxophilic late transition metal catalysts are used for these reactions, we suspect that the reductive condensation processes we develop may proceed at exceptionally low catalyst loading (less than 0.05 mol percent) and not suffer from complications involving catalyst poisoning by polyoxygenated substrates.