21034-29-7Relevant academic research and scientific papers
An access to highly enantioenrichedcis-3,5-disubstituted γ-lactones from α-bromoacetate and silyl enol ether
Kim, Seo Yun,Lee, Ha Rim,Park, Min Ji,Park, Yong Sun
, p. 7655 - 7663 (2021/09/22)
A novel synthetic strategy for highly enantioenrichedcis-3,5-disubstituted γ-lactones has been developed by the AgOTf-promoted nucleophilic substitution of α-bromoacetates with silyl enol ethers and subsequent reductive lactonization. The utility of this synthetic method was further demonstrated through the concise stereodivergent synthesis ofcis- andtrans-2,4-disubstituted tetrahydrofurans.
Cobalt-catalyzed annulation of styrenes with α-bromoacetic acids
Nguyen, Tung T.,Ngo, Bao H. T.,Le, Huy X.,Vu, Linh N. P.,To, Tuong A.,Phan, Anh N. Q.,Phan, Nam T. S.
, p. 5451 - 5455 (2021/02/12)
We report a method for addition of α-bromophenylacetic acids to vinyl C-C bonds in styrenes to afford γ-lactones. Reactions employed a simple cobalt catalyst Co(NO3)2·6H2O in the presence of dipivaloylmethane (dpm) ligand.
One-Pot Quinine-Catalyzed Synthesis of α-Chiral γ-Keto Esters: Enantioenriched Precursors of cis-α,γ-Substituted-γ-Butyrolactones
Meninno, Sara,Volpe, Chiara,Lattanzi, Alessandra
, p. 2845 - 2848 (2016/09/13)
A highly enantioselective one-pot synthesis of important building blocks, α-chiral γ-keto esters, has been developed by combining a quinine-catalyzed Michael addition of malononitrile to trans-enones followed by magnesium monoperoxyphthalate (MMPP) oxidat
Efficient addition of acid enediolates to epoxides
Gil, Salvador,Torres, Mercedes,Ortuzar, Natalia,Wincewicz, Richard,Parra, Margarita
, p. 2160 - 2165 (2007/10/03)
We report new conditions to facilitate the addition of dianions of carboxylic acids to epoxides as an alternative method to the use of aluminum enolates. These conditions require the use of a sub-stoichiometric (10%) amount of amine for dianion generation and the previous activation of the epoxide with LiCl. Other Lewis acids have been shown to be less effective. Yields are good but only low diastereoselectivity is attained, which has not been controlled despite attempts at optimization. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
LACTONIZATION OF PHENYLCYCLOPROPANECARBOXYLIC ACIDS
Sychkova, L. D.,Kharitonova, O. V.,Shabarov, Yu. S.
, p. 1298 - 1301 (2007/10/02)
The capacity of phenylcyclopropanecarboxylic acids for lactonization under the influence of mineral acids was studied.It was found that concentrated sulfuric acid at 20 deg C can give rise to lactonization only in the case where the intermediately formed carbocation is stabilized by a phenyl group.Preliminary isomerization to the corresponding unsaturated acid does not occur here.
