Catalytic Asymmetric [3 + 2] Cycloaddition Reaction between Aurones and Isocyanoacetates: Access to Spiropyrrolines via Silver Catalysis.

J Org Chem

School of Pharmaceutical Sciences and Chongqing Key Laboratory of Natural Product Synthesis and Drug Research , Chongqing University, 55 Daxuecheng South Road , Shapingba, Chongqing 401331 , People's Republic of China.

Published: September 2018

The first enantioselective formal [3 + 2] cycloaddition of aurone analogues with isocyanoacetates was developed via chiral Ag-complex catalysis. A variety of optically enriched spiro-1-pyrrolines were obtained in excellent yields, diastero- and enantioselectivities (up to 99% yield, >20:1 dr, >99% ee). This synthetic approach represents an extremely simple, efficient, and atom-economical method for spiro-1-pyrrolines synthesis.

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http://dx.doi.org/10.1021/acs.joc.8b01622DOI Listing

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