Tetrahedron

Radical cyclisations of imines and hydrazones

WR Bowman, PT Stephenson, NK Terrett, AR Young

Index: Bowman, W. Russell; Stephenson, Peter T.; Terrett, Nicholas K.; Young, Adrian R. Tetrahedron, 1995 , vol. 51, # 29 p. 7959 - 7980

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Citation Number: 66

Abstract

Radical cyclisation of sp3 carbon-centred radicals onto imines and hydrazones provides a new method for the synthesis of 5-and 6-membered ring nitrogen heterocycles. Cyclisation onto the electrophilic carbon of the C= N group and 5-exo stereoelectronic selectivity are the dominating mechanistic parameters. The C-centred radical intermediates were generated from benzeneselenyl precursors using Bu3SnH.