Enantioselective Formal [3+2] Cycloaddition of Epoxides with Imines under Brønsted Base Catalysis: Synthesis of 1,3‐Oxazolidines with Quaternary Stereogenic Center DOI
Azusa Kondoh,

Shiori Akahira,

Masafumi Oishi

и другие.

Angewandte Chemie, Год журнала: 2018, Номер 130(21), С. 6407 - 6411

Опубликована: Апрель 12, 2018

Abstract The formal [3+2] cycloaddition of epoxides and unsaturated compounds is a powerful methodology for the synthesis densely functionalized five‐membered heterocyclic containing oxygen. Described novel enantioselective under Brønsted base catalysis. bis(guanidino)iminophosphorane as chiral organosuperbase catalyst enabled reaction β , γ ‐epoxysulfones with imines, owing to its strong basicity high stereocontrolling ability, provide enantioenriched 1,3‐oxazolidines having two stereogenic centers, including quaternary one, in highly diastereo‐ manner.

Язык: Английский

Enantioselective [3+2] Cycloaddition of Donor‐Acceptor Aziridines and Imines to Construct 2,5‐trans‐Imidazolidines DOI

Jianglin Qiao,

Shiyu Wang, Xiaohua Liu

и другие.

Chemistry - A European Journal, Год журнала: 2023, Номер 29(18)

Опубликована: Янв. 5, 2023

An enantioselective [3+2] cycloaddition of donor-acceptor aziridines with N-aryl protected imines was developed a Ni(ClO4 )2 ⋅ 6H2 O/N,N'-dioxide catalyst system, providing broad range chiral trans-substituted imidazolidine compounds good yields and excellent enantioselectivities (up to 99 % yield, up 98 ee). Control experiments indicated that the products could offer diastereoselectivities control Ni(II)-N,N'-dioxide complex interaction substrates. The possible catalytic process proposed rationalize stereocontrol.

Язык: Английский

Процитировано

4

Recent Advances in Cycloaddition Reactions of Donor-Acceptor Aziridines via Carbon-Carbon Bond Cleavage DOI Open Access
Zuliang Chen,

Yingjing Wei,

Junliang Zhang

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2023, Номер 43(9), С. 3078 - 3078

Опубликована: Янв. 1, 2023

There are two different ring-opening modes of aziridines: aziridines via carbon-nitrogen bond cleavage, and carbon-carbon cleavage.Among them, the reaction cleavage has been reported in many reviews.The cycloaddition reactions donor-acceptor (D-A) recent 20 years mainly summarized.Under some proper catalysts, D-A yield azomethine ylides, which can undergo [3+n] with aldehydes, imines, alkenes, alkynes, indoles etc.

Язык: Английский

Процитировано

4

Five-Membered Ring Systems With O and N Atoms DOI
Franca M. Cordero, Donatella Giomi, Luisa Lascialfari

и другие.

Progress in heterocyclic chemistry, Год журнала: 2017, Номер unknown, С. 353 - 382

Опубликована: Янв. 1, 2017

Язык: Английский

Процитировано

11

TfOH-catalyzed formal [3+2] cycloaddition of N-tosylaziridine dicarboxylates and nitriles: Synthesis of tetrafunctionalized 2-imidazolines DOI

Qinglu Zuo,

Zhichao Shi, Feng Zhan

и другие.

Tetrahedron Letters, Год журнала: 2019, Номер 61(10), С. 151576 - 151576

Опубликована: Дек. 30, 2019

Язык: Английский

Процитировано

10

Enantioselective Formal [3+2] Cycloaddition of Epoxides with Imines under Brønsted Base Catalysis: Synthesis of 1,3‐Oxazolidines with Quaternary Stereogenic Center DOI
Azusa Kondoh,

Shiori Akahira,

Masafumi Oishi

и другие.

Angewandte Chemie, Год журнала: 2018, Номер 130(21), С. 6407 - 6411

Опубликована: Апрель 12, 2018

Abstract The formal [3+2] cycloaddition of epoxides and unsaturated compounds is a powerful methodology for the synthesis densely functionalized five‐membered heterocyclic containing oxygen. Described novel enantioselective under Brønsted base catalysis. bis(guanidino)iminophosphorane as chiral organosuperbase catalyst enabled reaction β , γ ‐epoxysulfones with imines, owing to its strong basicity high stereocontrolling ability, provide enantioenriched 1,3‐oxazolidines having two stereogenic centers, including quaternary one, in highly diastereo‐ manner.

Язык: Английский

Процитировано

10