Devarie-Baez Nelmi O, Kim Won-Suk, Smith Amos B, Xian Ming
Department of Chemistry, Washington State University, Pullman, Washington 99164, USA.
Org Lett. 2009 Apr 16;11(8):1861-4. doi: 10.1021/ol900434k.
Effective, one-pot syntheses of 2,3-disubstituted furans and thiophenes, exploiting 2-tert-butyldimethylsilyl-3-formylfuran and -thiophene as the respective bifunctional linchpins, have been developed. The synthetic protocol involves multicomponent type II Anion Relay Chemistry (ARC) mediated by a solvent-controlled C(sp(2))-->O 1,4-Brook rearrangement. Simple organolithiums and alpha-disubstituted ester enolates prove effective as the initiating nucleophiles.
利用2-叔丁基二甲基甲硅烷基-3-甲酰基呋喃和噻吩作为各自的双功能关键组分,已开发出有效合成2,3-二取代呋喃和噻吩的一锅法。该合成方案涉及由溶剂控制的C(sp(2))→O 1,4-布鲁克重排介导的多组分II型阴离子中继化学(ARC)。简单的有机锂和α-二取代酯烯醇盐被证明是有效的起始亲核试剂。