63506-92-3Relevant academic research and scientific papers
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.
α-Alkylidene-γ-butyrolactone synthesis via one-pot C-H insertion/olefination: substrate scope and the total synthesis of (±)-cedarmycins A and B
Lloyd, Matthew G.,D'Acunto, Mariantonietta,Taylor, Richard J.K.,Unsworth, William P.
, p. 7107 - 7123 (2015/02/19)
Abstract A system for the synthesis of α-alkylidene-γ-butyrolactones via a one-pot C-H insertion/olefination sequence is described. The process is based on the rhodium catalysed C-H insertion reaction of α-diazo-α-(diethoxyphosphoryl)acetates. The mild reaction conditions, operational simplicity and ready availability of starting materials are all key features. A wide range of successful reaction systems are reported (41 examples) highlighting the generality of the method. The application of this method in the total synthesis of the natural products (±)-cedarmycins A and B is also described.
A one-pot C-H insertion/olefination sequence for the formation of α-alkylidene-γ-butyrolactones
Lloyd, Matthew G.,Taylor, Richard J. K.,Unsworth, William P.
supporting information, p. 2772 - 2775 (2014/06/09)
A one-pot C-H insertion/olefination sequence for the conversion of α-diazo-α-(dialkoxyphosphoryl)acetates into α-alkylidene- γ-butyrolactones is reported. The key C-H insertion process is achieved using a catalytic amount of a dirhodium carboxylate cataly
α-ALKYLIDENE-γ-LACTONE SYNTHESIS: α-METHYL AND α-BENZYLCINNAMIC ACID DIANION ADDITION TO KETONES
Carlson, Robert M.,DeLane, James C.,Liu, Tian-lin
, p. 657 - 662 (2007/10/02)
α-methyl and α-benzylcinnamic acids and lithium diisopropylamide (DIPA) generate stable dianions that as addition reagents are useful for the synthesis of α-methylene- and α-benzylidene-γ-lactones.
