Abstract
An effective and stereoselective synthesis of 3-(1′-methyl/phenylallyl)-3-phenylthio-β-lactams (3/4) using substituted allylsilane and Lewis acid is described. The reaction leads to the formation of a mixture of C-3 substituted allyl β-Lactams. However, these compounds on desulphurisation using tri-n-butyltinhydride and Raney Ni provide two separable diastereomers of the reduced product.
In the presence of TiCl4, silanes such as crotylsilanes and cinnamylsilanes add efficiently at C-3 position of trans-3-chloro-3-phenylthio-β-lactams.
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Acknowledgements
We gratefully acknowledge the financial support for this work from TEQIP-II, UIET, P.U. Chandigarh, India.
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All additional information pertaining to characterization of the representative compounds (3a, 4a, 5a, 6a, 7a, 8a, 9a, 10a and 11a) using1H NMR and13C NMR techniques (Figures S1–S8) are given in the supporting information. Supplementary Information is available at www.ias.ac.in/chemsci.
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THAPAR, R., RESHMA & BARI, S.S. Studies towards C-3 functionalization of β-lactams using substituted allylsilanes. J Chem Sci 128, 1745–1753 (2016). https://doi.org/10.1007/s12039-016-1161-6
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DOI: https://doi.org/10.1007/s12039-016-1161-6