Cross-Dimerization of 2,5-Dihydrofuran with Conjugated Dienes Catalyzed by (Chiral Diene)ruthenium(0) Complexes and Origins of the Enantioselectivity

Hirano, Masafumi; Machida, Shuhei; Abe, Ryota; Mishina, Takuya; Komine, Nobuyuki; Wu, Hsyueh Liang

doi:10.1021/acs.organomet.1c00368

Cited by 4 publications

(3 citation statements)

References 53 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the reaction of 2,5-dihydrofuran with conjugated dienes, the enantioselectivity was low with chiral diene ligands L16d and L6a and was improved by using pseudo- C 2 -symmetric diene ligand L4a . The reaction with 2-phenyl-1,3-butadiene gave a mixture of regioisomeric products 384 (41%, 34% ee) and 385 (48%, 91% ee) (Scheme b) …”

Section: Applications Of Chiral Diene Ligands In Asymmetric Catalysismentioning

confidence: 99%

See 1 more Smart Citation

Chiral Diene Ligands in Asymmetric Catalysis

Huang

Hayashi

2022

Chem. Rev.

View full text Add to dashboard Cite

Asymmetric catalysis has emerged as a general and powerful approach for constructing chiral compounds in an enantioselective manner. Hence, developing novel chiral ligands and catalysts that can effectively induce asymmetry in reactions is crucial in modern chemical synthesis. Among such chiral ligands and catalysts, chiral dienes and their metal complexes have received increased attention, and a great progress has been made over the past two decades. This review provides comprehensive and critical information on the essential aspects of chiral diene ligands and their importance in asymmetric catalysis. The literature covered ranges from August 2003 (when the first effective chiral diene ligand for asymmetric catalysis was reported) to October 2021. This review is divided into two parts. In the first part, the chiral diene ligands are categorized according to their structures, and their preparation methods are summarized. In the second part, their applications in asymmetric transformations are presented according to the reaction types.

show abstract

Section: Applications Of Chiral Diene Ligands In Asymmetric Catalysismentioning

confidence: 99%

“…The reaction with 2-phenyl-1,3-butadiene gave a mixture of regioisomeric products 384 (41%, 34% ee) and 385 (48%, 91% ee) (Scheme 82b). 305…”

Section: Miscellaneous Asymmetric Reactionsmentioning

confidence: 99%

Chiral Diene Ligands in Asymmetric Catalysis

Huang

Hayashi

2022

Chem. Rev.

View full text Add to dashboard Cite

show abstract

“…Interestingly, when dimethyl acrylamide ( 3d ) and styrene ( 3e ) were used for the coupling partners of 2b , the corresponding 1,5-dienes (2 E ,6 E )- 6bd (64%) and (1 E ,5 E )- 6be (79%) were obtained, respectively. We have recently reported the enantioselective cross-dimerization of a conjugated diene with 2,5-dihydrofuran ( 3f ), but the treatment of 2b with 3f diastereoselectively gave rac -(( R , E ), S )- 7bf in a moderate yield (see Supporting Information). No cross-dimer products were obtained by the treatment with methyl methacrylate, acrolein, ( E )-hex-4-en-3-one, and triethoxyvinylsilane.…”

Section: Resultsmentioning

confidence: 99%

Ru(0)-Catalyzed Regioselective Synthesis of Borylated-1,4- and -1,5-Diene Building Blocks

et al. 2022

Self Cite

View full text Add to dashboard Cite

A new methodology for preparation of borylated-1,4-and -1,5-diene building blocks is established. Ru(0)-catalyzed cross-dimerization of (1E,3E)-penta-1,3-dien-1-ylboronic acid pinacolate ester (2b) with but-3-en-2-one (3a) selectively gives a borylated-1,4-diene product, (3E,6E)-5-methyl-(4,4,5,5-tetrameth-) also gives a borylated-1,4-diene product. These crossdimerizations give mono-borylated-1,4-dienes, yet cross-dimerizations using (1E,3E)-penta-1,3-dien-1-ylboronic acid pinacolate ester (2b) with vinyl B(dan) (3i) produce a diborylated-1,5diene. Selective formation of 1,6-diborylated-1,5-dienes is unprecedented, and a series of diborylated-1,5-dienes can be used as building blocks for Suzuki−Miyaura cross-coupling reactions. As an application of the present method, the formal synthesis of racbongkrekic acid, a strong inhibitor of the adenine nucleotide translocator, has been achieved.

show abstract