DOI: 10.1021/acs.orglett.6c04092 ISSN: 1523-7060
Base-Promoted Ring Opening of Bicyclo[1.1.0]butanes for Diastereoselective Hydroalkynylthiolation
Sujoy Saha, Aaron Taites, Kiran, Ravi KumarAbstract
Herein, we disclose a transition-metal-free base-promoted syn-selective hydroalkynylthiolation of bicyclo[1.1.0]butanes (BCBs) under mild conditions. The reaction involves the in situ formation of the alkylnylthiolate anion from readily available 1,2,3-thiadiazoles in the presence of a base, which adds to bicyclo[1.1.0]butanes (BCBs) to release the strain. The broad substrate scope, good functional group compatibility, applicability in late-stage derivatization of bioactive molecules, downstream product transformations, and scale-up synthesis demonstrate the synthetic potential of the present method.