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Synthesis of 6- and 7-Membered N-Heterocycles Using α-Phenylvinylsulfonium Salts

Johnathan V. Matlock, Thomas D. Svejstrup, Pradip Songara, Sarah Overington, Eoghan M. McGarrigle* and Varinder K. Aggarwal*

*University College Dublin, Belfield, Dublin 4, Ireland; University of Bristol, Cantock’s Close, BS8 1TS, Bristol, U.K., Email: eoghan.mcgarrigleucd.ie, v.aggarwalbristol.ac.uk

J. V. Matlock, T. D. Svejstrup, P. Songara, S. Overington, E. M. McGarrigle, V. K. Aggarwal, Org. Lett., 2015, 17, 5044-5047.

DOI: 10.1021/acs.orglett.5b02516 (free Supporting Information)


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Abstract

The reaction of 1,2-amino alcohols or diamines with an α-phenylvinylsulfonium salt enables a concise synthesis of stereodefined C-substituted morpholines and piperazines in very good yields. Factors affecting regio- and diastereocontrol are discussed. Azepines and oxazepines can also be prepared in moderate yields.

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Key Words

morpholines


ID: J54-Y2015