Advanced Synthesis and Catalysis
Advanced Synthesis and Catalysis
5 years ago

A Polystyrene-Supported Phase-Transfer Catalyst for Asymmetric Michael Addition of Glycine-Derived Imines to α,β-Unsaturated Ketones

A Polystyrene-Supported Phase-Transfer Catalyst for Asymmetric Michael Addition of Glycine-Derived Imines to α,β-Unsaturated Ketones
Shū Kobayashi, Hiroyuki Miyamura, Javier Miguélez
A 2-oxopyrimidinium salt was immobilized onto a polystyrene-derived polymer to generate a heterogeneous catalyst that effectively promoted the asymmetric Michael addition of glycine-derived imines to α,β-unsaturated ketones. The reactions proceeded smoothly to afford the desired adducts, (S)-tert-butyl 2-[(diarylmethylidene)amino]-5-oxoalkanoates, in high yields and with high enantioselectivities (up to 92% ee). The polymer catalyst could be recovered and reused at least five times without significant loss of activity or selectivity.

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

DOI: 10.1002/adsc.201700155

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