Enantioselective (3+2)-Annulation of β-Keto Esters with Azoalkenes towards Bicyclic Dihydropyrroles via Cooperative Palladium and Brønsted Acid Catalysis DOI
Christoph Schneider,

Till Friedmann,

Daniel A. Mireles-Chávez

и другие.

Synlett, Год журнала: 2023, Номер 35(09), С. 997 - 1000

Опубликована: Ноя. 13, 2023

Abstract A cooperative catalytic process through palladium and Brønsted acid activation is developed for the conjugate addition of cyclic β-keto esters to azoalkenes directly followed by hemiaminal formation upon cyclization. This transformation enabled utilizing chiral Pd-aqua complexes as combined acid–base catalysts. Thus, bicyclic highly functionalized dihydropyrroles with two contiguous quaternary stereogenic centers are formed in excellent yields single diastereomers exceptional enantioselectivity.

Язык: Английский

Alkylation of Phenols with 4,6-Di-tert-butyl-3-methoxymethylcatechol. Antiradical Activity of Sterically Hindered Catecholphenols DOI
Anastasiya E. Tarakanova,

Н. Д. Анисимова,

D. A. Martynova

и другие.

Russian Journal of General Chemistry, Год журнала: 2023, Номер 93(S3), С. S629 - S638

Опубликована: Дек. 1, 2023

Язык: Английский

Процитировано

2

New Developments of Chiral Palladium‐Aqua Complexes as Cooperative Brønsted Acid‐Base Catalysts in Organic Synthesis DOI Creative Commons

Cornelius V. Gärtner,

Christoph Schneider

ChemCatChem, Год журнала: 2023, Номер 15(10)

Опубликована: Апрель 12, 2023

Abstract Based upon their exceptional reactivity as cooperative Brønsted acid‐base catalysts chiral diphosphane Pd‐aqua complexes have successfully been utilized in a broad range of asymmetric transformations. Originally discovered by Sodeoka 25 years ago, they readily form reactive Pd enolates deprotonation β‐dicarbonyl compounds and simultaneously, acid liberated from the catalyst activates electrophile. After initial report some ensuing papers had published early 2000s, field lay dormant for more than decade. In recent years, however, new developments towards enantioselective synthesis various heterocycles other useful evolved which take advantage unique properties complexes.

Язык: Английский

Процитировано

1

Stereoselective Construction of Vicinal Quaternary Stereocenters via the 1,6-Conjugate Addition of β,β-Disubstituted N-Sulfinyl Metalloenamines to Isatin-Derived para-Quinone Methides DOI
Chong‐Dao Lu,

Zheng-Fei Li

Synthesis, Год журнала: 2023, Номер 56(05), С. 828 - 850

Опубликована: Дек. 6, 2023

Abstract A 1,6-conjugate addition reaction of β,β-disubstituted N-tert-butanesulfinyl metalloenamines, generated via stereospecific α-deprotonation enantioenriched α,α-disubstituted ketimines or deprotonation the NH in geometry-defined enesulfinamides, with isatin-derived para-quinone methides is developed to build vicinal quaternary stereocenters high stereocontrol. The resulting 3,3-disubstituted oxindoles contain a less-accessible acyclic stereogenic carbon substituted two sterically and electronically similar groups at α-position imino group. This protocol constitutes rare example stereoselective construction conjugate enolates/aza-enolates bearing β-substituents.

Язык: Английский

Процитировано

1

Recent Progress on NHC‐Catalyzed 1,6‐Conjugate Addition Reactions DOI
Jun Sun, Shichun Jiang,

Yonggui Liu

и другие.

The Chemical Record, Год журнала: 2024, Номер unknown

Опубликована: Окт. 17, 2024

Abstract As a significant variant of the Michael reaction, 1,6‐addition reaction has undergone considerable development over past decade. This effective strategy enables synthesis variety novel and potentially bioactive functional molecules. In this review, we summarize recent progress in NHC‐catalyzed reactions, highlighting their efficiency rapid complex We also provide our perspectives on future dynamic highly active research area.

Язык: Английский

Процитировано

0

Enantioselective (3+2)-Annulation of β-Keto Esters with Azoalkenes towards Bicyclic Dihydropyrroles via Cooperative Palladium and Brønsted Acid Catalysis DOI
Christoph Schneider,

Till Friedmann,

Daniel A. Mireles-Chávez

и другие.

Synlett, Год журнала: 2023, Номер 35(09), С. 997 - 1000

Опубликована: Ноя. 13, 2023

Abstract A cooperative catalytic process through palladium and Brønsted acid activation is developed for the conjugate addition of cyclic β-keto esters to azoalkenes directly followed by hemiaminal formation upon cyclization. This transformation enabled utilizing chiral Pd-aqua complexes as combined acid–base catalysts. Thus, bicyclic highly functionalized dihydropyrroles with two contiguous quaternary stereogenic centers are formed in excellent yields single diastereomers exceptional enantioselectivity.

Язык: Английский

Процитировано

0