Cascade Reaction of Donor-Acceptor Cyclopropanes: Mechanistic Studies on Cycloadditions with Nitrosoarenes and cis-Diazenes

被引：58
|
作者：
Chidley, Tristan [1 ]
Vemula, Naresh [1 ]
Carson, Cheryl A. [1 ]
Kerr, Michael A. [1 ]
Pagenkopf, Brian L. [1 ]
机构：
[1] Univ Western Ontario, Dept Chem, 1151 Richmond St, London, ON N6A 5B7, Canada
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 12期
基金：
加拿大自然科学与工程研究理事会;
关键词：
DIASTEREOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; 3+2 DIPOLAR CYCLOADDITION; FORMAL 4+2 CYCLOADDITION; NITRONES; ALKALOIDS; CYCLOBUTANES; TETRAHYDRO-1,2-OXAZINES; ANNULATIONS; DERIVATIVES;
D O I：
10.1021/acs.orglett.6b01269
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Tandem ring opening, elimination, and cycloaddition of donor-acceptor cyclopropanes were observed in Yb(OTf)(3)-catalyzed cycloaddition with nitrosoarenes. The reaction results in formation of tetrahydro-1,2-oxazine instead of the normal cycloadduct isoxazolidine via in situ nitrone formation. A similar cascade sequence was observed with cis-diazines. Mechanistic studies on this unique transformation offer an entirely new approach for reaction design with donor-acceptor cyclopropanes.
引用
收藏
页码：2922 / 2925
页数：4
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