502636-13-7Relevant academic research and scientific papers
Pd-Catalyzed Acyl C-O Bond Activation for Selective Ring-Opening of α-Methylene-β-lactones with Amines
Malapit, Christian A.,Caldwell, Donald R.,Sassu, Nicole,Milbin, Samuel,Howell, Amy R.
, p. 1966 - 1969 (2017)
A Pd-catalyzed ring-opening of β-lactones with various types of amines (primary, secondary, and aryl) to provide β-hydroxy amides with excellent selectivity toward acyl C-O bond cleavage is reported. The utility of this protocol is demonstrated in an asym
Strain-Driven Dyotropic Rearrangement: A Unified Ring-Expansion Approach to α-Methylene-γ-butyrolactones
Lei, Xiaoqiang,Li, Yuanhe,Lai, Yang,Hu, Shengkun,Qi, Chen,Wang, Gelin,Tang, Yefeng
supporting information, p. 4221 - 4230 (2020/12/22)
An unprecedented strain-driven dyotropic rearrangement of α-methylene-β-lactones has been realized, which enables the efficient access of a wide range of α-methylene-γ-butyrolactones displaying remarkable structural diversity. Several appealing features of the reaction, including excellent efficiency, high stereospecificity, predictable chemoselectivity and broad substrate scope, render it a powerful tool for the synthesis of MBL-containing molecules of either natural or synthetic origin. Both experimental and computational evidences suggest that the new variant of dyotropic rearrangements proceed in a dualistic pattern: while an asynchronous concerted mechanism most likely accounts for the reactions featuring hydrogen migration, a stepwise process involving a phenonium ion intermediate is favored in the cases of aryl migration. The great synthetic potential of the title reaction is exemplified by its application to the efficient construction of several natural products and relevant scaffolds.
Unusual, strained heterocycles: 3-Alkylidene-2-methyleneoxetanes from Morita-Baylis-Hillman-type adducts
Martinez, Isamir,Andrews, Alexander E.,Emch, Joseph D.,Ndakala, Albert J.,Wang, Jun,Howell, Amy R.
, p. 399 - 402 (2007/10/03)
(Matrix presented) 3-Alkylidene-2-methyleneoxetanes have been prepared by treating α-alkylidene-β-lactones, derived from Morita-Baylis-Hillman-type adducts, with dimethyltitanocene. Preliminary studies of the reactivity of these little known, strained het
