American Chemical Society
ol5b01644_si_002.cif (469.56 kB)

Direct Catalytic Asymmetric Conjugate Addition of Saturated and Unsaturated Thioamides

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posted on 2015-07-02, 00:00 authored by Nilanjana Majumdar, Akira Saito, Liang Yin, Naoya Kumagai, Masakatsu Shibasaki
Direct catalytic asymmetric conjugate addition of thiolactams to α,β-unsaturated thioamides was efficiently promoted by a soft Lewis acid/hard Brønsted base cooperative catalyst in a highly stereocontrolled manner. Thioamide functionality was crucial to promote both the efficient enolization of thiolactam pronucleophiles and the subsequent stereoselective conjugate addition to α,β-unsaturated thioamides. Differential manipulation of the two thioamide functionalities of the product highlights the synthetic utility of the present catalytic system.