Lewis Base-Catalyzed [4+3] Annulation of ortho-Quinone Methides and MBH Carbonates: Synthesis of Functionalized Benzo[b]oxepines Bearing Oxindole Scaffolds

被引:64
作者
Du, Ji-Yuan [1 ]
Ma, Yan-Hua [1 ]
Meng, Fan-Xiao [1 ]
Zhang, Rui-Rui [1 ]
Wang, Ruo-Nan [1 ]
Shi, Hong-Liang [1 ]
Wang, Qi [1 ]
Fan, Ya-Xin [1 ]
Huang, Hong-Li [1 ]
Cui, Ji-Chun [1 ]
Ma, Chun-Lin [1 ]
机构
[1] Liaocheng Univ, Coll Chem & Chem Engn, Liaocheng 252059, Shandong, Peoples R China
关键词
BAYLIS-HILLMAN CARBONATES; ONE-POT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; CYCLOADDITION REACTION; ASYMMETRIC-SYNTHESIS; O-QUINODIMETHANES; ALLENIC ESTERS; DERIVATIVES; ISATINS; ACCESS;
D O I
10.1021/acs.orglett.8b03709
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel Lewis base-catalyzed [4 + 3] annulation process for the construction of benzo[b]oxepine scaffolds has been developed. 1,4-Diazabicyclo[2.2.2]octane (DABCO) promotes the union of o-QMs and Morita-Baylis-Hillman carbonates in reasonable to excellent yields and good stereoselectivities (dr > 20:1). This straightforward, catalytic approach offers access to a variety of synthetically useful benzo[b]oxepine derivatives bearing oxindole scaffolds containing all-carbon spiro-quaternary stereocenters.
引用
收藏
页码:465 / 468
页数:4
相关论文
empty
未找到相关数据