期刊
ACS CATALYSIS
卷 9, 期 10, 页码 9259-9264出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b03656
关键词
Carbonyl-olefin metathesis; hydrazines; chromenes; cycloaddition; cycloreversion
资金
- National Institutes of Health (NIH) [R35 GM127135]
The catalytic ring-closing carbonyl-olefin metathesis (RCCOM) of O-allyl salicylaldehydes to form 2H-chromenes is described. The method utilizes a [2.2.1]-bicyclic hydrazine catalyst and operates via a [3 + 2]/retro-[3 + 2] metathesis manifold. The nature of the allyl substitution pattern was found to be crucial, with sterically demanding groups such as adamantylidene or diethylidene offering optimal outcomes. A survey of substrate scope is shown along with a discussion of mechanism supported by DFT calculations. Steric pressure arising from syn-pentane minimization of the diethylidene moiety is proposed to facilitate cycloreversion.
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