476429-08-0Relevant articles and documents
Catalytic Asymmetric Darzens-Type Epoxidation of Diazoesters: Highly Enantioselective Synthesis of Trisubstituted Epoxides
Jeong, Hye-Min,Nam, Dong Guk,Ryu, Do Hyun,Shim, Su Yong
supporting information, p. 22236 - 22240 (2021/09/13)
Highly enantioselective Darzens-type epoxidation of diazoesters with glyoxal derivatives was accomplished using a chiral boron–Lewis acid catalyst, which facilitated asymmetric synthesis of trisubstituted α,β-epoxy esters. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in high yield (up to 99 %) with excellent enantio- and diastereoselectivity (up to >99 % ee and >20:1 dr, respectively). The synthetic potential of this method was illustrated by conversion of the products to various compounds such as epoxy γ-butyrolactone, tertiary β-hydroxy ketone and epoxy diester.
Cu(I)/chiral bisoxazoline-catalyzed enantioselective sommelet-hauser rearrangement of sulfonium ylides
Wang, Jianbo,Li, Shu-Sen
supporting information, p. 12343 - 12358 (2020/11/10)
Catalytic asymmetric thia-Sommelet-Hauser rearrangement of sulfonium ylides remains a great challenge due to its multistep reaction mechanism involving metal carbene formation, proton transfer, and [2,3]-sigmatropic rearrangement. In particular, the key problem of such reactions is the differentiation of the enantiotopic lone pair electrons of sulfur, which generates the sulfonium ylide intermediate bearing chirality on the sulfur atom. With a modified chiral bisoxazoline ligand, we developed a Cu(I)- catalyzed asymmetric thia-Sommelet-Hauser rearrangement with good to excellent enantioselectivities. Mechanistic studies provide insights into the details of the reaction mechanism.
Three-Component Synthesis of Isoquinoline Derivatives by a Relay Catalysis with a Single Rhodium(III) Catalyst
Zhou, Chao,Jiang, Jijun,Wang, Jun
supporting information, p. 4971 - 4975 (2019/09/03)
A rhodium(III)-catalyzed one-pot three-component reaction of N-methoxybenzamide, α-diazoester, and alkyne was developed, providing an alternative way to synthesize isoquinoline derivatives. Mechanistically, it is a relay catalysis, and the reaction occurred via successive O-alkylation and C-H activation processes, both of which were promoted by the same catalyst.
PYRIDINE COMPOUNDS FOR CONTROLLING PHYTOPATHOGENIC HARMFUL FUNGI
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Page/Page column 131, (2018/04/20)
The present invention relates to compounds of formula I wherein the variables are defined as given in the description and claims. The invention further relates to uses and composition for compounds of formula I.
Palladium-catalyzed α-arylation of zinc enolates of esters: Reaction conditions and substrate scope
Hama, Takuo,Ge, Shaozhong,Hartwig, John F.
, p. 8250 - 8266 (2013/09/24)
The intermolecular α-arylation of esters by palladium-catalyzed coupling of aryl bromides with zinc enolates of esters is reported. Reactions of three different types of zinc enolates have been developed. α-Arylation of esters occurs in high yields with i
Efficient synthesis of α-aryl esters by room-temperature palladium-catalyzed coupling of aryl halides with ester enolates
Jorgensen, Morten,Lee, Sunwoo,Liu, Xiaoxiang,Wolkowski, Joanna P.,Hartwig, John F.
, p. 12557 - 12565 (2007/10/03)
A catalytic amount of Pd(dba)2 ligated by either carbene precursor N,N′-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazolium (1) or P(t-Bu)3 mediated the coupling of aryl halides and ester enolates to produce α-aryl esters in high yields at room temperature. The reaction was highly tolerant of functionalities and substitution patterns on the aryl halide. Improved protocols for the selective monoarylation of tert-butyl acetate and the efficient arylation of α,α-disubstituted esters were developed with LiNCy2 as base and P(t-Bu)3 as ligand. In addition, tert-butyl esters, such as those of Naproxen and Flurbiprofen, were prepared from tert-butyl propionate and aryl bromides in high yields in the presence of Pd(dba)2 and the hindered, saturated heterocyclic carbene ligand precursor.
