Abstract

Expedient nonclassical reaction of acetylenes with ketones: controlling the switch between bicyclic ketals and cyclopentenols formation

Highlights

  • The development of new reactions leading to the formation of C-C and C-O bonds, constructing biologically and pharmaceutically important structures via a single-reactor methodology, represents a long-standing challenge of fine organic synthesis

  • Fundamental organic synthesis has revealed a diversity of reactions of alkynes, which provide new C-C, C-N, and C-O bond formation, e.g. in important biomolecules as pyrroles,[6,7] pyridines,[2,8,9,10] vitamins A and E,1,11 β-carotene,[11] linalool,[11] citral,[12] steroids,[13,14] etc

  • We have recently shown that the one-pot assembly of 3-methyl-7-methylene-1,5-diphenyl6,8-dioxabicyclo[3.2.1]octane[24,25,26,27] from acetophenone

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Summary

Introduction

The development of new reactions leading to the formation of C-C and C-O bonds, constructing biologically and pharmaceutically important structures via a single-reactor methodology, represents a long-standing challenge of fine organic synthesis. A similar change of the products ratio up to 50:50 occurs by affecting the catalytic activity of the KOH/DMSO system via the reaction temperature decrease from 70 to 30 °C (entries 1-4), the conversion of acetophenone 1a expectedly drops from 100 to 46%.

Results
Conclusion

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