Stereospecific syn-dichlorination of allylic amines enabled by identification of a superior stereo-directing group DOI Creative Commons
Jeong Kyun Im, Jun‐Ho Choi, Won‐jin Chung

и другие.

Communications Chemistry, Год журнала: 2024, Номер 7(1)

Опубликована: Ноя. 26, 2024

Alteration of a well-established reaction mechanism for access to different molecular structures is an inherently intriguing research subject. In that context, syn-stereospecific alkene dihalogenation draws attention as long-standing problem in synthetic organic chemistry. The simplest approach would be the incorporation additional stereo-inverting step within traditional anti-dihalogenation process. Surprisingly, this seemingly trivial idea turned out challenging, and no suitable stereo-directing group was known before our work. Herein, we describe highly efficient syn-dichlorination N-protected allylic amines through anchimeric assistant phenomenon has been inapplicable dihalogenation. Upon rational identification superior stereo-director, 1,8-naphthalimide, practical conditions with mild convenient dichlorinating reagents can accommodate formerly unemployable aryl alkenes excellent yields (>95%) stereospecificity (>50:1). DFT calculation suggests concerted internal trapping without discrete carbocationic species, which accounts conservation stereochemical integrity. Vicinal anti-stereospecific under conventional conditions, however, remains less explored. Here, authors identify 1,8-naphthalimide stereo-director achieve stereospecificity.

Язык: Английский

A stereodivergent multicomponent approach for the synthesis of C–N atropisomeric peptide analogues DOI Creative Commons

Natalie J. Roper,

Aaron D. G. Campbell, Paul G. Waddell

и другие.

Chemical Science, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Four-component reactions at room temperature delivered C–N atropisomeric peptide analogues possessing both central and axial chirality with complete diastereocontrol. Reactions elevated selectively afforded the other diastereoisomer.

Язык: Английский

Процитировано

3
General Alkene 1,2-syn-Cyano-Hydroxylation Procedure Via Electrochemical Activation of Isoxazoline Cycloadducts DOI Creative Commons

Taciano A. S. Wanderley,

Roberto Buscemi,

Órla Conboy

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(47), С. 32848 - 32858

Опубликована: Ноя. 13, 2024

Stereoselective alkene 1,2-difunctionalization is a privileged strategy to access three-dimensional C(sp

Язык: Английский

Процитировано

1
Stereospecific syn-dichlorination of allylic amines enabled by identification of a superior stereo-directing group DOI Creative Commons
Jeong Kyun Im, Jun‐Ho Choi, Won‐jin Chung

и другие.

Communications Chemistry, Год журнала: 2024, Номер 7(1)

Опубликована: Ноя. 26, 2024

Alteration of a well-established reaction mechanism for access to different molecular structures is an inherently intriguing research subject. In that context, syn-stereospecific alkene dihalogenation draws attention as long-standing problem in synthetic organic chemistry. The simplest approach would be the incorporation additional stereo-inverting step within traditional anti-dihalogenation process. Surprisingly, this seemingly trivial idea turned out challenging, and no suitable stereo-directing group was known before our work. Herein, we describe highly efficient syn-dichlorination N-protected allylic amines through anchimeric assistant phenomenon has been inapplicable dihalogenation. Upon rational identification superior stereo-director, 1,8-naphthalimide, practical conditions with mild convenient dichlorinating reagents can accommodate formerly unemployable aryl alkenes excellent yields (>95%) stereospecificity (>50:1). DFT calculation suggests concerted internal trapping without discrete carbocationic species, which accounts conservation stereochemical integrity. Vicinal anti-stereospecific under conventional conditions, however, remains less explored. Here, authors identify 1,8-naphthalimide stereo-director achieve stereospecificity.

Язык: Английский

Процитировано

0