Transition-metal-free synthesis of polysubstituted pyrrole derivatives <i>via</i> cyclization of methyl isocyanoacetate with aurone analogues
作者:Zhi-Peng Wang、Yun He、Pan-Lin Shao
DOI:10.1039/c8ob01558a
日期:——
Presented herein is an unprecedented transition-metal-free cyclization of methyl isocyanoacetate with aurone analogues catalyzed by NaOH. Various 2,3,4-trisubstituted pyrroles were obtained in excellent yields (up to 99%). The high efficiency of this synthetic procedure, coupled with the operational simplicity and atom economy, makes it an attractive method for the synthesis of polysubstituted pyrroles
Catalytic Asymmetric [3 + 2] Cycloaddition Reaction between Aurones and Isocyanoacetates: Access to Spiropyrrolines via Silver Catalysis
作者:Zhi-Peng Wang、Sichuan Xiang、Pan-Lin Shao、Yun He
DOI:10.1021/acs.joc.8b01622
日期:2018.9.21
The first enantioselective formal [3 + 2] cycloaddition of aurone analogues with isocyanoacetates was developed via chiral Ag-complex catalysis. A variety of optically enriched spiro-1-pyrrolines were obtained in excellent yields, diastero- and enantioselectivities (up to 99% yield, >20:1 dr, >99% ee). This synthetic approach represents an extremely simple, efficient, and atom-economical method for
[3 + 2] Cycloaddition of Azaoxyallyl Cations with Cyclic Ketones: Access to Spiro-4-oxazolidinones
作者:Pan-Lin Shao、Zi-Rui Li、Zhi-Peng Wang、Ming-Hui Zhou、Qi Wu、Ping Hu、Yun He
DOI:10.1021/acs.joc.7b01728
日期:2017.10.6
The first formal [3 + 2] cycloaddition reaction of in situ generated azaoxyallyl cation with cyclic ketones has been developed using mild reaction conditions. A variety of spiro-4-oxazolidinones was obtained in excellent yields (up to 99%). The high efficiency of this process, coupled with the operational simplicity, makes it an attractive method for the synthesis of spiro-4-oxazolidinones.
diastereomeric series of benzofuran‐fused δ‐lactams and dihydropyridines in nearly perfect stereoselectivity (d.r. >20:1, >99 % ee for all examples). The complementarity of N‐heterocycliccarbene and chiral amine as the catalyst was demonstrated for the first time, together with an excellent level of catalytic efficiency (1 mol % loading).
Design of Aurone‐Based Dual‐State Emissive (DSE) Fluorophores
作者:Daria V. Berdnikova、Sören Steup、Michael Bolte、Markus Suta
DOI:10.1002/chem.202300356
日期:——
Aurone derivatives were introduced as easily accessible dual-state emissive (DSE) fluorophores along with the description of molecular design principles. Facile one-step synthesis in combination with biological activities make DSEaurones unique tool for biomedical applications.