Yb(OTf)3 catalyzed [1,3]-rearrangement of 3-alkenyl oxindoles.

Abstract

A Yb(OTf)3 catalyzed [1,3]-rearrangement of 3-alkenyl oxindoles was achieved, affording a variety of multifunctional 3-ylideneoxindoles with good yields and Z/E selectivities (64%-89% yield, 78 : 22->99 : 1 Z/E). Importantly, an operationally simple, one-pot sequential catalytic synthesis of 3-ylideneoxindoles was also developed. Additionally, a cross [1,3]-rearrangement experiment and nonracemic transformation were also carried out, which indicated a concerted rearrangement mechanism of this methodology.