Tetrahedron Letters

Iodine (III)-promoted synthesis of oxazolines from N-allylamides

NG Moon, AM Harned

Index: Moon, Nicholas G.; Harned, Andrew M. Tetrahedron Letters, 2013 , vol. 54, # 23 p. 2960 - 2963

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Citation Number: 24

Abstract

PhI (OAc) 2 (activated by BF3· OEt2) has been used to promote the oxidative cyclization of N- allylamides to give oxazolines. The reaction products are formed in high yield and, when a branched allylic amine is used, high diastereoselectivity. Initial mechanistic experiments suggest that the final C–O bond is formed from a reactive tight ion pair, rather than a neutral external nucleophile.