1021925-45-0Relevant academic research and scientific papers
Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes
R?se, Philipp,Emge, Steffen,Yoshida, Jun-Ichi,Hilt, Gerhard
, p. 174 - 183 (2015)
The cobalt(I)-catalysed 1,4-hydrovinylation reaction of allyloxytrimethylsilane and allyl alcohol with substituted 1,3-dienes leads to hydroxy-functionalised 1,4-dienes in excellent regio- and diastereoselective fashion. Those 1,4-dienols can be converted
Z-Selective Dienylation Enables Stereodivergent Construction of Dienes and Unravels a Ligand-Driven Mechanistic Dichotomy
Dang, Hang T.,Nguyen, Viet D.,Haug, Graham C.,Vuong, Ngan T. H.,Arman, Hadi D.,Larionov, Oleg V.
, p. 1042 - 1052 (2021)
The development of stereoselective and efficient reactions for the construction of conjugated dienes and polyenes has remained at the forefront of organic chemistry, due to their key roles in medicinal chemistry, organic synthesis, and material science. The synthesis of conjugated dienes and polyenes is typically accomplished in a multistep manner by the sequential installation of individual Ca?C bonds because it allows for control of stereoselectivity and efficiency of formation of each double bond. A conceptually distinct dienylation approach entails a stereoselective appendage of a four-carbon unit, shortcutting diene synthesis. Dienylation with sulfolene provided a direct route to E-dienes, but the synthesis of substantially more challenging Z-dienes remained elusive. Here, we report that a highly Z-selective dienylation can now be achieved by a simple adjustment of a ligand, enabling stereodivergent synthesis of E- A nd Z-dienes from one reagent and in one step. A detailed mechanistic investigation of the E- A nd Z-selective dienylation provided insight into the divergent behavior of the two catalytic systems and revealed that differences in relative stabilities of catalytically active palladium phosphine complexes have a major impact on the stereochemical outcomes of the dienylation.
Selective 1,2-Aminoisothiocyanation of 1,3-Dienes Under Visible-Light Photoredox Catalysis
Guo, Weisi,Wang, Qian,Zhu, Jieping
supporting information, p. 4085 - 4089 (2020/12/25)
Selective three-component 1,2-diamination of 1,3-dienes with concurrent introduction of two orthogonally protected amino groups remains unknown despite its significant synthetic potential. We report herein that reaction of conjugated dienes with N-aminopy
Ni-Catalyzed Site-Selective Dicarboxylation of 1,3-Dienes with CO2
Tortajada, Andreu,Ninokata, Ryo,Martin, Ruben
supporting information, p. 2050 - 2053 (2018/02/19)
A site-selective catalytic incorporation of multiple CO2 molecules into 1,3-dienes en route to adipic acids is described. This protocol is characterized by its mild conditions, excellent chemo- and regioselectivity and ease of execution under CO2 (1 atm), including the use of bulk butadiene and/or isoprene feedstocks.
