Department of Chemistry, Wayne State University , 5101 Cass Avenue, Detroit, Michigan 48202, United States.
Department of Chemistry, The University of Alabama , Tuscaloosa, Alabama 35487, United States.
Org Lett. 2016 Dec 2;18(23):6098-6101. doi: 10.1021/acs.orglett.6b03088. Epub 2016 Nov 10.
A comparison study of the Ru(II)-catalyzed rearrangements of allenyl- and alkynylcyclopropanols to the corresponding cyclopentenones has been undertaken with the aid of an alkyl substituent on the three-membered ring. These ring expansion reactions proceed with exceptional regioselectivity irrespective of the cis/trans stereochemistry of the substituents on the three-membered ring. β-Carbon elimination is the common feature in the absence of a chelating group at the 4'-position in the alkyne chain.
在三员环上引入一个烷基取代基，对 Ru(II)催化的烯丙基和炔丙基环丙醇重排为相应的环戊烯酮进行了对比研究。这些环扩张反应具有极好的区域选择性，与三员环上取代基的顺/反立体化学无关。在炔烃链的 4'位没有螯合基团的情况下，β-碳原子消除是常见的特征。
