Asymmetric (4+3) and (4+1) Annulations of Isatin-derived Morita-Baylis-Hillman Carbonates to Construct Diverse Chiral Heterocyclic Frameworks

被引：84
作者：
Yan, Ru-Jie [1 ,2 ]
Liu, Bao-Xin [1 ,2 ]
Xiao, Ben-Xian [1 ,2 ]
Du, Wei [1 ,2 ]
Chen, Ying-Chun [1 ,2 ,3 ]
机构：
[1] Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, West China Sch Pharm, Minist Educ, Chengdu 610041, Peoples R China
[2] Sichuan Univ, Sichuan Res Ctr Drug Precis Ind Technol, West China Sch Pharm, Chengdu 610041, Peoples R China
[3] Third Mil Med Univ, Coll Pharm, Chongqing 400038, Peoples R China
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 11期
关键词：
DONOR-ACCEPTOR CYCLOBUTANES; FORMAL 3+2+2 CYCLOADDITION; MBH CARBONATES; LEWIS-BASE; IMINES; ALKYNES; ACCESS; ENALS;
D O I：
10.1021/acs.orglett.0c01283
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A chiral tertiary amine-catalyzed asymmetric gamma-regioselective (4 + 3) annulation reaction of isatin-derived Morita-Baylis-Hillman carbonates and 1-azadienes was developed, delivering chiral azepane spirooxindoles with excellent stereoselectivity. In addition, by tuning the substituents of Morita-Baylis-Hillman carbonates, the switchable gamma-(4 + 3) or alpha-(4 + 1) annulation reaction with o-quinone methides was observed to furnish benzo[b]oxepines or 2,3-dihydrobenzofurans, respectively, under similar catalytic conditions.
引用
收藏
页码：4240 / 4244
页数：5
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