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An Aminocatalyzed Stereoselective Strategy for the Formal α‐Propargylation of Ketones
Author(s) -
Jurberg Igor D.
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701433
Subject(s) - scope (computer science) , conjugate , stereoselectivity , combinatorial chemistry , formal synthesis , ketone , sequence (biology) , chemistry , computer science , organic chemistry , catalysis , mathematics , programming language , mathematical analysis , biochemistry
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.