Nucleophile-Controlled Regiodivergent Domino Reactions of Enetriones with γ-Bromocrotonates: Access to 1,3-Dienic Esters and Tetrasubstituted Pyrans DOI

Dan Xiong,

Sen Zhang, Zhiyue Li

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 23, 2025

Herein, we developed an efficient nucleophile-controlled regiodivergent domino reaction between enetriones and γ-bromocrotonates. This method allowed for the rapid synthesis of a range 1,3-dienic esters tetrasubstituted pyrans under metal-free conditions. In presence pyridine, SN2 substitution/Michael addition/elimination sequence formed in satisfactory yields with high E-stereoselectivities. Alternatively, addition/cyclization/cyclopropanation/cyclopropane ring-opening process forged good help Et3N. It is interesting to note that site-selective reactions γ-bromocrotonates at α- or γ-position were readily realized by modulating pyridine Furthermore, simple Et3N act as both nucleophiles substitution Lewis bases deprotonation processes.

Язык: Английский

Stereoselective Synthesis of Atropisomeric Amides Enabled by Intramolecular Acyl Transfer DOI Creative Commons
Jack M. Wootton,

Natalie J. Roper,

C. Morris

и другие.

Chemical Science, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

A stereoselective strategy to make C–N atropisomeric amides based on intramolecular acyl transfer via a tethered Lewis basic pyridine or tertiary amine group is reported.

Язык: Английский

Процитировано

0
Nucleophile-Controlled Regiodivergent Domino Reactions of Enetriones with γ-Bromocrotonates: Access to 1,3-Dienic Esters and Tetrasubstituted Pyrans DOI

Dan Xiong,

Sen Zhang, Zhiyue Li

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 23, 2025

Herein, we developed an efficient nucleophile-controlled regiodivergent domino reaction between enetriones and γ-bromocrotonates. This method allowed for the rapid synthesis of a range 1,3-dienic esters tetrasubstituted pyrans under metal-free conditions. In presence pyridine, SN2 substitution/Michael addition/elimination sequence formed in satisfactory yields with high E-stereoselectivities. Alternatively, addition/cyclization/cyclopropanation/cyclopropane ring-opening process forged good help Et3N. It is interesting to note that site-selective reactions γ-bromocrotonates at α- or γ-position were readily realized by modulating pyridine Furthermore, simple Et3N act as both nucleophiles substitution Lewis bases deprotonation processes.

Язык: Английский

Процитировано

0