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Base-Mediated Divergent Synthesis of Spiro-heterocycles Using Pronucleophiles and Ethylene via Thianthrenation. | LitMetric

Base-Mediated Divergent Synthesis of Spiro-heterocycles Using Pronucleophiles and Ethylene via Thianthrenation.

Org Lett

International Collaborative Laboratory of 2D Materials for Optoelectronics Science and Technology of Ministry of Education, Institute of Microscale Optoelectronics, Shenzhen University, Shenzhen 518060, P. R. China.

Published: July 2024

Spirocyclic compounds are abundant in biologically active products. However, the divergent synthesis of spirocyclic compounds using low-cost and abundant available starting materials remains a challenge. Herein, we report an effective method for producing spirocyclic motifs using a cyclic β-carbonyl ester or amide and ethylene via thianthrenation. This strategy highlights the exciting possibility of utilizing abundant ethylene as a C-2 synthon and allows regulating the core structure of the spirocyclic compound by simply altering the base type.

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http://dx.doi.org/10.1021/acs.orglett.4c01435DOI Listing

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