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

Asymmetric Synthesis of Pyrrolidine-Containing Chemical Scaffolds via Tsuji–Trost Allylation of N-tert-Butanesulfinyl Imines

Asymmetric Synthesis of Pyrrolidine-Containing Chemical Scaffolds via Tsuji–Trost Allylation of N-tert-Butanesulfinyl Imines
Irene Georgiou, William Lewis, Ross P. Wilkie, Robert A. Stockman, Rafid S. Dawood
A simple and efficient asymmetric synthesis of novel sp3-rich pyrrolidine chemical scaffolds over five steps starting from simple ketones is described. Key steps involve the use of tert-butanesulfinamide as a chiral auxiliary to perform an asymmetric Tsuji–Trost allylation, with subsequent cross-metathesis with an acrylate ester and reduction of the sulfinimine/cyclisation of the resulting amine giving the pyrrolidine scaffolds in high yields and diastereoselectivites. By removing the chiral auxiliary and functionalising the ester group, the resulting scaffold core can be further derivatised. Three is the magic number: Use of the chiral tert-butane sulfinyl directing group allows installation of three stereogenic centres in three separate reactions with control of chirality, and a rapid entry into highly sp3-rich three-dimensional bicyclic pyrrolidine chemical scaffolds.

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

DOI: 10.1002/chem.201702616

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