Double isomerization of oxetane amides to azetidine esters with ring expansion and contraction

S Kanoh, T Nishimura, Y Kita, H Ogawa…

Index: Kanoh, Shigeyoshi; Nishimura, Tomonari; Kita, Yukiko; Ogawa, Hiroshi; Motoi, Masatoshi; Takani, Masako; Tanaka, Toshiyuki Journal of Organic Chemistry, 2000 , vol. 65, # 7 p. 2253 - 2256

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Citation Number: 28

Abstract

Oxetane has been long known as a cyclic ether possessing ring-opening polymerizability, 1 and the cationic polymerization has been developed as a broadly applicable method for synthesizing functionalized polyethers. 2, 3 An interesting exception to this generally accepted concept was found by Corey et al. in ortho ester (5) synthesis by the Lewis acid catalyzed isomerization of oxetane esters (4)(eq 3 in Scheme 1). 4 Thereafter, we have ...