Origin of Regio‐ and Stereoselectivity in the NHC‐catalyzed Reaction of Alkyl Pyridinium with Aliphatic Enal
Sign Up to like & getrecommendations! Published in 2019 at "ChemCatChem"
DOI: 10.1002/cctc.201901965
Abstract: The mechanisms of N‐heterocyclic carbene (NHC)‐catalyzed dearomatization reaction of alkyl pyridinium have been intensively studied using the density functional theory (DFT) method. The chemoselectivity and stereoselectivity were both analyzed based on the established mechanisms. The… read more here.
Keywords: nhc catalyzed; alkyl pyridinium; reaction alkyl; stereoselectivity ... See more keywords
Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC‐Catalyzed Kinetic Resolution
Sign Up to like & getrecommendations! Published in 2021 at "European Journal of Organic Chemistry"
DOI: 10.1002/ejoc.202100491
Abstract: An oxidative NHC-catalyzed kinetic resolution (KR) of racemic mixtures is presented. The developed reaction furnishes tricyclic dihydropyranones with three contiguous stereocenters in excellent dia- and enantioselectivity, with good-to-moderate yields. Mechanistic studies indicate that the rate-determining… read more here.
Keywords: three contiguous; kinetic resolution; dihydropyranones three; catalyzed kinetic ... See more keywords
NHC-Catalyzed Cascade Reaction between β-Methyl Enals and Dienones for Quick Construction of Complex Multicyclic Lactones.
Sign Up to like & getrecommendations! Published in 2020 at "Organic letters"
DOI: 10.1021/acs.orglett.0c00533
Abstract: A NHC-promoted cascade reaction between β-methyl enal and dienone is developed for quick access to multicyclic lactone molecules bearing quaternary chiral carbon centers. Our study constitutes the first 1,6-addition of the acylazolium vinyl enolate γ-carbon… read more here.
Keywords: cascade reaction; nhc catalyzed; reaction methyl; catalyzed cascade ... See more keywords
NHC-Catalyzed Enantioselective [3 + 3] Annulation to Construct 5,6-Dihydropyrimidin-4-ones.
Sign Up to like & getrecommendations! Published in 2020 at "Organic letters"
DOI: 10.1021/acs.orglett.0c02832
Abstract: The unprecedented enantioselective NHC-catalyzed [3 + 3] annulation of α-bromoenals with amidines via a dual C-N bond formation is described. The protocol allows a rapid preparation of 5,6-dihydropyrimidinones in acceptable yields with good enantioselectivities. read more here.
Keywords: annulation; construct dihydropyrimidin; nhc catalyzed; catalyzed enantioselective ... See more keywords
NHC-Catalyzed [3 + 3] Annulation of Thioamides and Modified Enals for the Enantioselective Synthesis of Functionalized Thiazinones.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.9b03188
Abstract: N-Heterocyclic carbene (NHC)-catalyzed [3 + 3] annulation of thioamides with modified enals allowing the enantioselective synthesis of functionalized 1,3-thiazin-4-ones is reported. The NHC generated from the chiral triazolium salt was optimal and the reaction is… read more here.
Keywords: nhc catalyzed; annulation thioamides; modified enals; thioamides modified ... See more keywords
Enantioselective NHC-Catalyzed [3+3] Annulation of α-Bromoenals with 2-Aminobenzimidazoles.
Sign Up to like & getrecommendations! Published in 2020 at "Organic letters"
DOI: 10.1021/acs.orglett.9b04054
Abstract: A chiral carbene-catalyzed [3+3] annulation of α-bromoenals with 2-aminobenzimidazoles providing pyrimido[1,2-a]benzimidazoles has been described. This protocol features a broad scope and good functional group tolerance. Biological studies indicated that the formed pyrimido[1,2-a]benzimidazole exhibited moderate cytotoxic… read more here.
Keywords: annulation bromoenals; bromoenals aminobenzimidazoles; nhc catalyzed; catalyzed annulation ... See more keywords
NHC-Catalyzed ε-Umpolung via p-Quinodimethanes and Its Nucleophilic Addition to Ketones
Sign Up to like & getrecommendations! Published in 2019 at "ACS Catalysis"
DOI: 10.1021/acscatal.9b04409
Abstract: An unprecedented NHC-catalyzed generation of p-quinodimethanes via e-umpolung of 4-(chloromethyl)benzaldehydes and the following e-addition to active ketones was developed. A series of active keton... read more here.
Keywords: catalyzed umpolung; via quinodimethanes; addition; nhc catalyzed ... See more keywords
NHC-Catalyzed Deamination of Primary Sulfonamides: A Platform for Late-Stage Functionalization.
Sign Up to like & getrecommendations! Published in 2019 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.8b11800
Abstract: Herein we describe the development and application of a method for the mild, late-stage conversion of primary sulfonamides to several other other functional groups. These reactions occur via initial reductive deamination of sulfonamides to sulfinates… read more here.
Keywords: late stage; nhc catalyzed; stage; catalyzed deamination ... See more keywords
Insights into N-heterocyclic carbene-catalyzed [3 + 4] annulation reactions of 2-bromoenals with N-Ts hydrazones
Sign Up to like & getrecommendations! Published in 2018 at "Organic chemistry frontiers"
DOI: 10.1039/c8qo00716k
Abstract: The possible mechanisms and the origin of the stereoselectivity of the N-heterocyclic carbene (NHC)-catalyzed [3 + 4] annulation reaction of 2-bromoenal with N-Ts hydrazone have been investigated using density functional theory (DFT). The general mechanism… read more here.
Keywords: annulation; annulation reactions; nhc catalyzed; reaction ... See more keywords
An NHC-catalyzed [3+2] cyclization of β-disubstituted enals with benzoyl cyanides.
Sign Up to like & getrecommendations! Published in 2022 at "Chemical communications"
DOI: 10.1039/d2cc04025e
Abstract: The NHC-catalyzed asymmetric [3+2] cyclization of benzoyl cyanides to homoenolate generated in situ from enals was reported. This methodology leads to the efficient construction of a series of chiral cyclic compounds bearing vicinal quaternary stereocenters… read more here.
Keywords: catalyzed cyclization; disubstituted enals; nhc catalyzed; benzoyl cyanides ... See more keywords
N-Heterocyclic carbene (NHC)-catalyzed oxidation of unactivated aldimines to amides via imine umpolung under aerobic conditions
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DOI: 10.1039/d2ra00897a
Abstract: Herein, we disclose an NHC-catalyzed aerobic oxidation of unactivated aldimines for the synthesis of amides via umpolung of imines proceeding through an aza-Breslow intermediate. We have developed an eco-friendly method for the conversion of imines… read more here.
Keywords: amides via; nhc catalyzed; unactivated aldimines; oxidation unactivated ... See more keywords