Novel Stereo‐Induction Pattern in Pudovik Addition/Phospha‐Brook Rearrangement Towards Chiral Trisubstituted Allenes DOI

Jia‐Yan Zheng,

Fan Wang, Yan Zhang

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(22)

Опубликована: Март 23, 2024

Abstract Despite the significance of chiral allene skeletons in catalysis, organic synthesis and medicinal chemistry et al., there is a scarcity reports on axially allenyl phosphorus compounds. Here, we disclosed an efficient straightforward cascade reaction between ethynyl ketones phosphine oxides, resulting broad array trisubstituted allenes incorporating moiety high yields with excellent stereoselectivities facilitated by peptide‐mimic phosphonium salt (PPS) Additionally, comprehensive series mechanistic experiments have been conducted to elucidate that this proceeds via asymmetric Pudovik addition followed subsequent phospha ‐Brook rearrangement occurs concomitantly kinetic resolution, representing stereospecific protonation process facilitating central‐to‐axial chirality transfer manner. We anticipate our research will pave way for promising exploration novel stereo‐induction pattern addition/ reaction.

Язык: Английский

Palladium-catalyzed allylic allenylation of homoallyl alcohols with propargylic carbonates DOI

Ping‐Xin Zhou,

Murong Wang,

Xiang Li

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(8), С. 2033 - 2038

Опубликована: Янв. 1, 2023

A palladium-catalyzed reaction of homoallyl alcohols with propargylic carbonates was realized via oxidative addition/decarboxylation/retro-allylation.

Язык: Английский

Процитировано

8

A Pd-catalyzed highly selective three-component protocol for trisubstituted allenes DOI Creative Commons
Can Li,

Zhengnan Zhou,

Shengming Ma

и другие.

Chemical Science, Год журнала: 2023, Номер 14(28), С. 7709 - 7715

Опубликована: Янв. 1, 2023

A novel three-component protocol to synthesize trisubstituted allenes from 2-alkynyl-1,4-diol dicarbonate with organoboronic acid and malonate has been developed.

Язык: Английский

Процитировано

8

Transition Metal‐Catalyzed Synthesis of 1,2,3,4‐Tetrasubstituted 1,3‐Dienes from Propargylic Esters DOI

Mengfu Dai,

Lucy Felicity Kabandula,

Lanzhu Tai

и другие.

ChemCatChem, Год журнала: 2024, Номер 16(14)

Опубликована: Янв. 24, 2024

Abstract Transition metal‐catalyzed synthesis of propargylic esters has been widely investigated, offering distinctive opportunities to build 1,3‐diene skeletons. Access 1,2,3,4‐tetrasubstituted 1,3‐dienes a longstanding challenge in organic due great diversity stereoisomers from four substituents and unpredictable regioselectivity. Given the synthetic challenges importance, inventing methods for generation this valuable architecture gathered much more attention. Recently, several intriguing works concerning topic have achieved towards high regio‐ stereoselective elaborate 1,3‐dienes. Herein, concept summarizes recent advances transition construction discusses mechanism as well their applications.

Язык: Английский

Процитировано

3

Cobalt(II)-Catalyzed Enantioselective Propargyl Claisen Rearrangement: Access to Allenyl-Substituted Quaternary β-Ketoesters DOI
Yaping Wang, Xingping Zhang, Ming‐Sheng Xie

и другие.

Organic Letters, Год журнала: 2023, Номер 25(39), С. 7105 - 7109

Опубликована: Сен. 21, 2023

Highly enantioselective propargyl Claisen rearrangement of O-propargyl β-ketoesters was achieved under 2.5 mol % the chiral cobalt complex as catalyst mild reaction conditions. With Co(OTf)2 Lewis acid and C1-symmetric imidazoline-pyrroloimidazolone pyridine ligand, diverse allenyl-substituted all-carbon quaternary were obtained in good yields (up to 97% yield) high enantioselectivities 98% ee).

Язык: Английский

Процитировано

7

Novel Stereo‐Induction Pattern in Pudovik Addition/Phospha‐Brook Rearrangement Towards Chiral Trisubstituted Allenes DOI

Jia‐Yan Zheng,

Fan Wang, Yan Zhang

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(22)

Опубликована: Март 23, 2024

Abstract Despite the significance of chiral allene skeletons in catalysis, organic synthesis and medicinal chemistry et al., there is a scarcity reports on axially allenyl phosphorus compounds. Here, we disclosed an efficient straightforward cascade reaction between ethynyl ketones phosphine oxides, resulting broad array trisubstituted allenes incorporating moiety high yields with excellent stereoselectivities facilitated by peptide‐mimic phosphonium salt (PPS) Additionally, comprehensive series mechanistic experiments have been conducted to elucidate that this proceeds via asymmetric Pudovik addition followed subsequent phospha ‐Brook rearrangement occurs concomitantly kinetic resolution, representing stereospecific protonation process facilitating central‐to‐axial chirality transfer manner. We anticipate our research will pave way for promising exploration novel stereo‐induction pattern addition/ reaction.

Язык: Английский

Процитировано

2