Chemistry - A European Journal
Chemistry - A European Journal
5 years ago

An Aminocatalyzed Stereoselective Strategy for the Formal α-Propargylation of Ketones

An Aminocatalyzed Stereoselective Strategy for the Formal α-Propargylation of Ketones
Igor D. Jurberg
A two-step reaction sequence is described for the asymmetric formal α-propargylation of ketones. This approach takes advantage of an aminocatalyzed conjugate addition of ketones to alkylidene isoxazol-5-ones, followed by a controlled nitrosative degradation event. The target compounds can be accessed in broad scope, in moderate to good yields, perfect diastereocontrol and good to excellent enantioselectivity. Add and unmask! Alkylidene isoxazol-5-ones can be used as key building blocks in a stereoselective aminocatalyzed Michael addition/nitrosative alkynylation sequence to produce an overall process of α-propargylation of ketones. This reaction sequence produces moderate to good yields, perfect diastereocontrol and good to excellent enantioselectivity, therefore making this synthetic route a viable strategy for the construction of densely substituted α-propargyl ketones.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701433

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