1459246-62-8Relevant articles and documents
Regioselective Organocatalytic Formation of Carbamates from Substituted Cyclic Carbonates
Sope?a, Sergio,Laserna, Victor,Guo, Wusheng,Martin, Eddy,Escudero-Adán, Eduardo C.,Kleij, Arjan W.
, p. 2172 - 2178 (2016)
A highly regioselective catalytic approach has been developed towards carbamates derived from cyclic organic carbonates by reaction of the latter with amine reagents under organocatalytic control. For various combinations of carbonate and amine substrates, an organocatalyst (TBD: 1,5,7-triazabicyclo[4.4.0]dec-5-ene) was used to increase the reaction kinetics while exerting excellent regioselective control. The current method is the first general approach towards the control over the regioselectivity of this reaction using a wide variety of easily accessed substituted organic carbonates. (Figure presented.) .
Palladium-Catalyzed Regio- And Stereoselective Cross-Coupling of Vinylethylene Carbonates with Ketimine Esters to Generate (Z)-Tri- And Tetra-substituted Allylic Amino Acid Derivatives
Chen, Fener,Huang, Guanxin,Ke, Miaolin,Liu, Zhigang,Tao, Yuan,Wang, Jiaqi
, p. 4135 - 4140 (2020)
Herein we report the palladium-catalyzed regio- and stereoselective cross-coupling of vinylethylene carbonates with ketimine esters to construct allylic amino acid scaffolds. This operationally simple protocol furnished (Z)-tri- and tetra-substituted ally
Palladium-catalyzed stereoselective (3 + 2) cycloaddition of vinylethylene carbonates with cyclicN-sulfonyl ketimines
Gao, Xing,Zhu, Dongyu,Jiang, Feng,Liao, Jianning,Wang, Wei,Wu, Yongjun,Zheng, Lufei,Guo, Hongchao
supporting information, p. 4877 - 4881 (2021/06/16)
A diastereoselective (3 + 2) cycloaddition ofN-sulfonyl ketimines with vinylethylene carbonates (VECs) in the presence of Pd2dba3·CHCl3and PPh3has been developed. The reaction of various substituted VECs and diverse cyclicN-sulfonyl ketimines proceeded smoothly under mild conditions, giving highly functionalized oxazolidine frameworks in good to excellent yields with moderate to good diastereoselectivities. With the use of spiroketal-based diphosphine SKP as a chiral ligand, an asymmetric version of the current (3 + 2) cycloaddition was achieved, and chiral products were obtained in >99% ee in most cases.
Asymmetric Synthesis of Multi-Substituted Tetrahydrofurans via Palladium/Rhodium Synergistic Catalyzed [3+2] Decarboxylative Cycloaddition of Vinylethylene Carbonates
Ming, Siliang,Qurban, Saira,Du, Yu,Su, Weiping
supporting information, p. 12742 - 12746 (2021/07/28)
Unlike the comprehensive development of tandem multi-metallic catalysis, bimetallic synergistic catalysis has been challenging to achieve high stereoselectivity with the generation of multi-stereogenic centers. Herein, an efficient synergistic catalysis for the diastereo- and enantioselective synthesis of multi-substituted tetrahydrofuran derivatives has been developed. Under mild reaction conditions, a series of target molecules with three consecutive stereocenters were synthesized by a palladium(0)/rhodium(III) bimetal-catalyzed asymmetric decarboxylative [3+2]-cycloaddition of vinylethylene carbonates with α,β-unsaturated carbonyl compounds. The corresponding adducts were obtained with moderate to high yields (67 %～98 %) and excellent stereoselectivities (>20 : 1 d.r., up to 99 % ee).
