6052-64-8Relevant articles and documents
Zinc-mediated α-regioselective Barbier-type cinnamylation reactions of aldehydes, ketones and esters
Zhao, Li-Ming,Gao, Hua-Shuai,Li, De-Feng,Dong, Jing,Sang, Lan-Lin,Ji, Jie
, p. 4359 - 4366 (2017/07/10)
We report a simple, efficient, and general method for the zinc-mediated regioselective cinnamylation of aldehydes and ketones under Barbier-type conditions in a one-pot synthesis affording the corresponding α-cinnamylated alcohols in moderate to excellent yields. Compared to the literature procedures, this approach is operationally simple, uses simple reactants, and provides direct access to linear α-cinnamylated alcohols with excellent regioselectivity. Experimental results suggest that the reactions proceed through the radical pathway. In addition, the reaction was found to be scalable to the gram-scale and the one-pot protocol is also applicable to less reactive esters leading to bishomoallylic alcohols which were valuable intermediates for desymmetrizing intramolecular Heck cyclization, allowing for the elaboration to functionalized building blocks.
α-Regioselective Barbier Reaction of Carbonyl Compounds and Allyl Halides Mediated by Praseodymium
Wu, San,Li, Ying,Zhang, Songlin
, p. 8070 - 8076 (2016/09/09)
The first utility of praseodymium as a mediating metal in the Barbier reaction of carbonyl compounds with allyl halides was reported in this paper. In contrast to the traditional metal-mediated or catalyzed Barbier reactions, exclusive α-adducts were obta