Choudhary Kavita, Deshpande Akanksha Santosh, Singh Vinod K
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur-208016, Uttar Pradesh, India.
Chem Commun (Camb). 2024 Aug 20;60(68):9062-9065. doi: 10.1039/d4cc02957g.
The first metal-catalyzed (2+4) annulation of 5-alkenyl thiazolones and α,α-dicyanoalkylidenes has been developed vinylogous Michael/cyclization/isomerization reaction. This (2+4) annulation reaction is catalyzed by a chiral Ag-()-DTBM-SEGPHOS catalyst, delivering enantioenriched spiro[cyclohexenamines-thiazolone] having contiguous quaternary and tertiary stereocenters in good to excellent yield (up to 80%) and excellent stereoselectivities (up to 97% ee and >20 : 1 dr). This methodology has high functional group tolerance and produces a broad range of enantioenriched products under mild reaction conditions.
首次开发了5-烯基噻唑酮与α,α-二氰基亚烷基的金属催化(2+4)环化反应，即乙烯基类似物迈克尔/环化/异构化反应。该(2+4)环化反应由手性Ag-()-DTBM-SEGPHOS催化剂催化，以良好至优异的产率（高达80%）和优异的立体选择性（高达97% ee和>20:1 dr）提供具有相邻季碳和叔碳立体中心的对映体富集的螺[环己烯胺-噻唑酮]。该方法具有高官能团耐受性，并且在温和的反应条件下可制备多种对映体富集的产物。
