Regiodivergent Synthesis of Spirocyclic Compounds through Pd-Catalyzed Regio- and Enantioselective [3+2] Spiroannulation

Barry M Trost; Zhijun Zuo

doi:10.1002/anie.202016439

Regiodivergent Synthesis of Spirocyclic Compounds through Pd-Catalyzed Regio- and Enantioselective [3+2] Spiroannulation

Angew Chem Int Ed Engl. 2021 Mar 8;60(11):5806-5810. doi: 10.1002/anie.202016439. Epub 2021 Feb 1.

Authors

Barry M Trost¹, Zhijun Zuo¹

Affiliation

¹ Department of Chemistry, Stanford University, Stanford, CA, 94305-5080, USA.

PMID: 33474803
DOI: 10.1002/anie.202016439

Abstract

A novel Pd⁰ -catalyzed highly regio- and enantioselective [3+2] spiroannulation reaction has been developed for rapid assembly of a new class of [5,5] spirocyclic carbo- and heterocycles. Notably, the regioselectivity could be dominated by fine-tuning of the Pd-π-allyl intermediate. An array of coupling partners could be well-tolerated with excellent regio-, and enantioselectivities. Moreover, the potential application of this reaction was exemplified by several further transformations.

Keywords: asymmetric catalysis; heterocycle; palladium; regioselectivity; spiroannulation.