Novel and Convenient Ozonating Approach to cis-Hydroxylation of Cyclic Vinylsilanes

Abstract

An efficient method for cis-hydroxylation of vinylsilanes under very mild and practical conditions using ozone in water as well as aqueous solvents is described.

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GRAPHICAL ABSTRACT

Keywords:

• Aqueous ammonium hydroxide
• cis-hydroxylation
• ozone
• silyl cycloalkenes
• silyl diols
• water

ACKNOWLEDGMENTS

We are thankful to Ch. Charan Singh University, Meerut (Uttar Pradesh), India, for providing the necessary research facilities. We are grateful to the analytical division of the Indian Institute of Technology, Delhi, for providing analytical and spectral data. In addition, we thank S. K. Yadav, head, Research and Development, Surya Pharmaceuticals Ltd., Chandigarh, India, for his advice during the course of this work.

Notes

^a Yield of isolated product.

^b Isolation problem.

^c 1a was used as input for all optimization studies and the optimized condition was applied to the rest of the compounds.

^a Substrate prepared as per reported literature.^{[ 7 ]}

^b Progress of reactions were monitored by thin-layer chromatography.

^c All compounds are known and identified by comparison with authentic samples.^{[ 5 , 6 ]}

^d All reaction performed in a mixture of THF/water (15:8).

^e Yields of isolated product.