Transformation of γ-ketoaldehyde acetals into 3-substituted-2-cyclopentenones via cyanophosphates under mild conditions

The reaction of cyanophosphates, which are readily derived from y-ketoaldehyde acetals, with TMSN3 (3 eq)/Bu2SnO (0.3 eq) in refluxing toluene directly furnished 3-substituted-2-cyclopentenones in modest to good yield under mild conditions. The present method was further applied toward the synthesis of dechlorotrichodenone C isolated from Trichoderma asperellum. (C) 2021 Elsevier Ltd. All rights reserved.

Automated summary

The reaction of cyanophosphates with TMSN3/Bu2SnO in refluxing toluene directly synthesized 3-substituted-2-cyclopentenones in modest to good yield under mild conditions. This method was also applied to the synthesis of dechlorotrichodenone C isolated from Trichoderma asperellum.