Chinese Chemical Letters, Год журнала: 2024, Номер 35(9), С. 109916 - 109916
Опубликована: Апрель 22, 2024
Язык: Английский
ACS Catalysis, Год журнала: 2024, Номер 14(6), С. 3812 - 3844
Опубликована: Фев. 23, 2024
Chiral skeletons with multiple stereogenic centers widely reside in nature and drugs, their relative absolute configuration often determine physiological or pharmacological properties. Stereodivergent synthesis of chiral molecules is not only great significance, but also highly challenging since the formation one diastereomers inherently preferred most asymmetric reactions. dual catalysis, introduced 2013 by Carreira group, perfectly catered to all requirements for full stereoselectivity control given reactions two catalysts are utilized a synergistic way act independently, has now been arguably efficient strategy realize stereodivergent synthesis. This comprehensive review presents an overview development enabled catalysis past ten years, providing readers fundamental attributes as well ability, scope, mechanism, limitations this strategy.
Язык: Английский
Процитировано
31
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(25)
Опубликована: Апрель 16, 2024
Aminocatalysis is a well-established tool that enables the production of enantioenriched compounds under mild conditions. Its versatility underscored by its seamless integration with various synthetic approaches. While combination aminocatalysis metal catalysis, photochemistry, and stoichiometric oxidants has been extensively explored, synergy electrochemical activation remains largely unexplored. Herein, we present successful merger electrochemistry to perform SOMO-type transformations, expanding toolkit for asymmetric synthesis. The methodology harnesses electricity drive oxidation catalytically generated enamines, which ultimately partake in enantioselective radical processes, leading α-alkylated aldehydes. Crucially, mechanistic studies highlight how this strategy enabled use redox shuttle, 4,4'-dimethoxybiphenyl, prevent catalyst degradation furnishing coveted good yield high enantioselectivity.
Язык: Английский
Процитировано
14
Journal of the American Chemical Society, Год журнала: 2024, Номер 146(13), С. 9404 - 9412
Опубликована: Март 20, 2024
The catalytic and enantioselective construction of quaternary (all-carbon substituents) stereocenters poses a formidable challenge in organic synthesis due to the hindrance caused by steric factors. One conceptually viable potentially versatile approach is coupling C–C bond through an outer-sphere mechanism, accompanied realization enantiocontrol cooperative catalysis; however, examples such processes are yet be identified. Herein, we present method for creating different compounds with photoredox/Fe/chiral primary amine triple catalysis. This facilitates connection unactivated alkyl source tertiary moiety, which also rare. scalable process exhibits mild conditions, does not necessitate use base, possesses good functional-group tolerance. Preliminary investigations into underlying mechanisms have provided valuable insights reaction pathway.
Язык: Английский
Процитировано
13
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(21)
Опубликована: Март 21, 2024
Abstract The construction of two distal stereocenters through a single catalytic process is great interest in organic synthesis. While there are some successful reports regarding stereodivergent preparation 1,3‐ or 1,4‐stereocenters, the more challenged 1,5‐nonadjacent have never been achieved fashion. Herein we describe synergistic palladium/copper catalysis for 1,4‐difunctionalization reactions 1,3‐dienes, providing access to quaternary stereocenters. Because each catalysts separately controlled one newly formed stereocenters, synthesis all four diastereomers products could readily be simply by choosing an appropriate combination chiral catalysts. Experimental and computational studies supported mechanism involving Heck/Tsuji–Trost cascade reaction, origins stereoselectivity were elucidated.
Язык: Английский
Процитировано
13
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(35)
Опубликована: Май 16, 2024
Abstract The construction of chiral motifs containing nonadjacent stereocenters in an enantio‐ and diastereoselective manner has long been a challenging task synthetic chemistry, especially with respect to their stereodivergent synthesis. Herein, we describe protocol that enables the 1,5/1,7‐nonadjacent tetrasubstituted through Pd/Cu‐cocatalyzed Heck cascade reaction. Notably, C=C bond relay strategy involving shift π‐allyl palladium intermediate was successfully applied asymmetric 1,7‐nonadjacent stereocenters. current method allows for efficient preparation molecules bearing two privileged scaffolds, oxindoles non‐natural α‐amino acids, good functional group tolerance. full complement four stereoisomers products could be readily accessed by simple combination metal catalysts different enantiomers.
Язык: Английский
Процитировано
10
Journal of the American Chemical Society, Год журнала: 2025, Номер unknown
Опубликована: Янв. 27, 2025
The absolute and relative configurations of bioactive chiral molecules are typically relevant to their biological properties. It is thus highly important desirable construct all possible stereoisomers a lead candidate or given natural compound. Synergistic dual catalysis has been recognized as reliable synthetic strategy for variety predictable stereodivergent transformations. Despite the impressive progress made in this field, carbon-carbon bond-formation reactions involving stabilized nucleophiles remain elusive. Herein, we report an iridium- magnesium-catalyzed one-pot sequential allylic alkylation/nucleophilic alkylation cascade process synthesis four 3,3'-disubstituted oxindoles through three-component reaction. A diverse array products readily prepared with high functional group compatibility good yields excellent diastereo- enantioselectivities. Subsequently, total spirooxindole alkaloid trigolutes B D accomplished concise unified route using same set starting materials.
Язык: Английский
Процитировано
1
ACS Catalysis, Год журнала: 2024, Номер 14(11), С. 8160 - 8167
Опубликована: Май 10, 2024
Rhodium(III)-catalyzed enantioselective C–H activation has emerged as a powerful tool for assembling enabling chiral molecules. However, this approach is significantly hampered by the cumbersome synthetic routes preparing rhodium catalysts. In sharp contrast, we herein report on an electrochemical domino catalysis system that exploits achiral Cp*-rhodium catalyst along with easily accessible Brønsted base activation/annulation reaction of alkenes benzoic acids. Our strategy offers environmentally benign and most user-friendly synthetically useful phthalides in good enantioselectivity, employing electricity sustainable oxidant.
Язык: Английский
Процитировано
7
Chemical Society Reviews, Год журнала: 2024, Номер 53(13), С. 6735 - 6778
Опубликована: Янв. 1, 2024
The review summarizes the increasing applications of chiral bisphosphine ligand Ph-BPE in catalytic asymmetric reactions past twenty years.
Язык: Английский
Процитировано
6
Organic Letters, Год журнала: 2024, Номер 26(41), С. 8956 - 8960
Опубликована: Окт. 7, 2024
We herein report the development of a novel Pd/Ni dual-catalyzed ring-opening functionalization
Язык: Английский
Процитировано
5
Chemical Science, Год журнала: 2024, Номер 15(26), С. 10135 - 10145
Опубликована: Янв. 1, 2024
A stereodivergent synthesis of chiral ζ-hydroxy amino esters containing 1,6-stereocenters and a unique β,γ-unsaturation was developed through asymmetric Cu/Ru relay catalysis to conduct the borrowing hydrogenation/1,6-Michael addition protocol.
Язык: Английский
Процитировано
4