- Zinc-mediated α-regioselective Barbier-type cinnamylation reactions of aldehydes, ketones and esters
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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.
- Zhao, Li-Ming,Gao, Hua-Shuai,Li, De-Feng,Dong, Jing,Sang, Lan-Lin,Ji, Jie
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p. 4359 - 4366
(2017/07/10)
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- Highly α-regioselective neodymium-mediated allylation of diaryl ketones
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The first utility of neodymium as a mediating-metal in the highly α-regioselective Barbier reaction of diaryl ketones with allyl halides is reported in this paper. This reaction was conveniently carried out under mild conditions in a one-pot fashion with
- Zhang, Fang,Wang, Ru,Wu, San,Wang, Peipei,Zhang, Songlin
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p. 87710 - 87718
(2016/09/23)
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- α-Regioselective Barbier Reaction of Carbonyl Compounds and Allyl Halides Mediated by Praseodymium
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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
- Wu, San,Li, Ying,Zhang, Songlin
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p. 8070 - 8076
(2016/09/09)
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- Pd-catalyzed nucleophilic allylic alkylation of aliphatic aldehydes by the use of allyl alcohols
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Under catalysis of Pd(OAc)2-(P-n-Bu)3, Et 2Zn promotes a variety of allyl alcohols to undergo nucleophilic allylation of aliphatic aldehydes and ketones at room temperature and provides homoallyl alcohols in 60-90 and ca. 60% isolated yield, respectively. The reaction is irreversible and kinetically controlled, and unique regio- and stereoselectivities observed for the allylation with unsymmetrically substituted allyl alcohols are discussed.
- Kimura, Masanari,Shimizu, Masamichi,Tanaka, Shuji,Tamaru, Yoshinao
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p. 3709 - 3718
(2007/10/03)
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