Highly Chemo- and Diastereoselective Construction of Quaternary Stereocenters through Palladium-Catalyzed [3 + 2] Cyclization of 5-Alkenyl Thiazolones.

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2019
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Abstract
We report a highly chemo- and diastereoselective [3 + 2] cyclization of vinylethylene carbonates and 5-alkenyl thiazolones through palladium catalysis. The previously inert aza-thioester moiety on the thiazolone substrates is reacted selectively with the zwitterionic π-allylpalladium species. A variety of amide monothioacetals (AMTA) with two quaternary stereocenters are facilely synthesized. An additional spirocyclic quaternary stereocenter could be further installed by Rh-catalyzed metal-carbene insertion into the C-S bond on the AMTA moiety in a highly stereoselective manner.
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Authors Liu, Yue;Huang, Qian-Wei;Li, Qing-Zhu;Leng, Hai-Jun;Dai, Qing-Song;Zeng, Rong;Liu, Yan-Qing;Zhang, Xiang;Han, Bo;Li, Jun-Long;
Journal Organic letters
Year 2019
DOI
10.1021/acs.orglett.9b02781
URL
Keywords
trace metals belgian coastal zone coastal environment diffusive gradients in thin-films lability

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