205108-18-5Relevant academic research and scientific papers
Crossed Regio- and Enantioselective Iron-Catalyzed [4+2]-Cycloadditions of Unactivated Dienes
Braconi, Elena,Cramer, Nicolai
, (2021/12/22)
The cyclohexene motif is ubiquitous in nature and specialty chemicals. A straightforward selective access to chiral cyclohexenes from unactivated dienes and dienophiles is not feasible by classical Diels–Alder reaction and constitutes an unsolved syntheti
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
Nickel-catalyzed allyl-allyl coupling reactions between 1,3-dienes and allylboronates
Ji, Ding-Wei,He, Gu-Cheng,Zhang, Wei-Song,Zhao, Chao-Yang,Hu, Yan-Cheng,Chen, Qing-An
supporting information, p. 7431 - 7434 (2020/07/15)
A regiospecific allyl-allyl coupling reaction between 1,3-dienes and allylboronates has been demonstrated under nickel catalysis. Salient features of this method include the earth-abundant metal catalyst, excellent regioselectivity and good functional group tolerance. Notably, even congested allyl substrates can also be applied to this protocol, thus allowing for the rapid preparation of a series of valuable 1,5-dienes. This journal is
Highly stereoselective and catalytic desulfitative C[sbnd]O and C[sbnd]I dienylation with sulfolenes: The importance of basic additives
Dang, Hang T.,Nguyen, Viet D.,Pham, Hoang H.,Arman, Hadi D.,Larionov, Oleg V.
supporting information, p. 3258 - 3264 (2019/04/14)
Conjugated dienes and polyenes are central structural motifs of natural products, and key synthetic intermediates in organic synthesis and materials science. We describe herein a palladium-catalyzed dienylation of aryl, heteroaryl, and vinyl triflates, nonaflates and iodides that were previously identified as recalcitrant substrates for the sulfolene-mediated catalytic dienylation. The method has now been successfully expanded to C[sbnd]O and C[sbnd]I dienylation, demonstrating broad scope with respect to sulfonates, iodides and sulfolenes. The reactions proceed with high regio- and stereoselectivity, and efficiency that are strongly influenced by basic additives, whose influence on the reaction performance was systematically studied.
Highly Regio- and Stereoselective Catalytic Synthesis of Conjugated Dienes and Polyenes
Nguyen, Vu T.,Dang, Hang T.,Pham, Hoang H.,Nguyen, Viet D.,Flores-Hansen, Carsten,Arman, Hadi D.,Larionov, Oleg V.
supporting information, p. 8434 - 8438 (2018/07/05)
Conjugated dienes and polyenes are typically synthesized by sequential introduction of C=C bonds. Here, we report a practical and scalable, catalytic dienylation that is highly regio- and stereoselective for both C=C bonds. The reaction is enabled by a stereoselective palladium-catalyzed cross-coupling that is preceded by a regioselective base-induced ring opening of readily available sulfolenes. The dienylation reaction is particularly useful for the synthesis of synthetically challenging dienes containing cis double bonds. We also show that the reaction can serve as a synthetic platform for the construction of conjugated polyenes.
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.
Cobalt-Catalyzed Carbonylative Cross-Coupling of Alkyl Tosylates and Dienes: Stereospecific Synthesis of Dienones at Low Pressure
Sargent, Brendon T.,Alexanian, Erik J.
supporting information, p. 12438 - 12440 (2017/09/25)
Despite advances in organometallic cross-coupling of alkyl electrophiles, there are few stereoselective reactions of chiral, nonracemic substrates. Herein we report a stereospecific carbonylative coupling of alkyl tosylates and dienes producing enantioenriched dienones. This catalytic process proceeds under low pressure and mild conditions using a simple cobalt catalyst and extends to diverse tosylate and diene coupling partners. The transformation constitutes a unique, convergent approach to the asymmetric synthesis of valuable carbonyl compounds from easily accessed starting materials.
Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles
Marcum, Justin S.,Roberts, Courtney C.,Manan, Rajith S.,Cervarich, Tia N.,Meek, Simon J.
supporting information, p. 15580 - 15583 (2017/11/14)
Catalytic enantioselective addition of N-heteroarenes to terminal and internal 1,3-dienes is reported. Reactions are promoted by 5 mol % of Rh catalyst supported by a new chiral pincer carbodicarbene ligand that delivers allylic substituted arenes in up to 95% yield and up to 98:2 er. Mechanistic and X-ray evidence is presented that supports that the reaction proceeds via a Rh(III)-η3-allyl.
Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst
Adamson, Nathan J.,Hull, Ethan,Malcolmson, Steven J.
, p. 7180 - 7183 (2017/06/05)
We report a method for the catalytic, enantioselective intermolecular addition of aliphatic amines to acyclic 1,3-dienes. In most cases, reactions proceed efficiently at or below room temperature in the presence of 5 mol % of a Pd catalyst bearing a PHOX ligand, generating allylic amines in up to 97:3 er. The presence of an electron-deficient phosphine within the ligand not only leads to a more active catalyst but also is critical for achieving high site selectivity in the transformation.
Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes
R?se, Philipp,Emge, Steffen,Yoshida, Jun-Ichi,Hilt, Gerhard
supporting information, p. 174 - 183 (2015/02/19)
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
