Theoretical investigation on diastereoselective [2+2] cycloaddition and Pd-catalyzed enantioselective [3+2] cycloaddition for synthesis of cis-β-lactam and exo-furobenzopyranone DOI Open Access
Nan Lü, Chengxia Miao, Xiaozheng Lan

и другие.

Thermal Science and Engineering, Год журнала: 2024, Номер 7(1), С. 5949 - 5949

Опубликована: Июнь 25, 2024

The mechanism is investigated for Wolff rearrangement/Staudinger [2+2] cycloaddition cascade and Pd-catalyzed, decarboxylative, formal [3+2] cycloaddition. rearrangement of 3-diazotetramic acid determined to be rate-limiting step generates cyclic acyl ketene. interaction ketene with imine firstly results in zwitterion followed by conrotatory cyclization giving major cis-β-lactam. For synthesis s-VECs, the epoxidation−cyclization hydrolysis give precursor better performing exocyclic derivative. reaction 3-cyanochromone includes decarboxylation, nucleophilic attack subsequent ring closure yielding 5-exo-trig furobenzopyranone. Based on comparison between possible paths, diastereoselectivity cis over trans regio-divergence 7-endo-trig are both kinetically controlled common. positive solvation effect suggested decreased absolute activation energies chlorobenzene chloroform solution compared gas. These supported Multiwfn analysis FMO composition specific TSs, MBO value vital bonding, breaking.

Язык: Английский

HFIP-driven Schmidt-type reaction enables chromone-3-carbonitriles and its applications DOI
Jia Xu, Jie Lei, Lixin Zhang

и другие.

Molecular Diversity, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 23, 2024

Язык: Английский

Процитировано

1
Theoretical investigation on diastereoselective [2+2] cycloaddition and Pd-catalyzed enantioselective [3+2] cycloaddition for synthesis of cis-β-lactam and exo-furobenzopyranone DOI Open Access
Nan Lü, Chengxia Miao, Xiaozheng Lan

и другие.

Thermal Science and Engineering, Год журнала: 2024, Номер 7(1), С. 5949 - 5949

Опубликована: Июнь 25, 2024

The mechanism is investigated for Wolff rearrangement/Staudinger [2+2] cycloaddition cascade and Pd-catalyzed, decarboxylative, formal [3+2] cycloaddition. rearrangement of 3-diazotetramic acid determined to be rate-limiting step generates cyclic acyl ketene. interaction ketene with imine firstly results in zwitterion followed by conrotatory cyclization giving major cis-β-lactam. For synthesis s-VECs, the epoxidation−cyclization hydrolysis give precursor better performing exocyclic derivative. reaction 3-cyanochromone includes decarboxylation, nucleophilic attack subsequent ring closure yielding 5-exo-trig furobenzopyranone. Based on comparison between possible paths, diastereoselectivity cis over trans regio-divergence 7-endo-trig are both kinetically controlled common. positive solvation effect suggested decreased absolute activation energies chlorobenzene chloroform solution compared gas. These supported Multiwfn analysis FMO composition specific TSs, MBO value vital bonding, breaking.

Язык: Английский

Процитировано

0