Diastereoselective synthesis of cyclopropane amino acids using diazo compounds generated in situ

…, J de Vicente, M Walter, WG Whittingham…

Index: Adams, Luke A.; Aggarwal, Varinder K.; Bonnert, Roger V.; Bressel, Bettina; Cox, Russell J.; Shepherd, Jon; De Vicente, Javier; Walter, Magnus; Whittingham, William G.; Winn, Caroline L. Journal of Organic Chemistry, 2003 , vol. 68, # 24 p. 9433 - 9440

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Citation Number: 64

Abstract

A simple and high-yielding method for the preparation of cyclopropane amino acids is described. The novel method involves the one-pot cyclopropanation of readily available dehydroamino acids using aryl and unsaturated diazo compounds generated in situ from the corresponding tosylhydrazone salts. It was found that thermal 1, 3-dipolar cycloaddition followed by nitrogen extrusion gave the cyclopropane amino acid derivatives with good E ...