硝酮与亲电乙烯碳烯中间体的非对映[3 + 3]环加成反应。
Asymmeric formal [3 + 3]-cycloaddition reactions of nitrones with electrophilic vinylcarbene intermediates.
机构信息
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
出版信息
J Am Chem Soc. 2011 Oct 19;133(41):16402-5. doi: 10.1021/ja207664r. Epub 2011 Sep 27.
Abstract
With metal carbene access to dipolar intermediates, 3,6-dihydro-1,2-oxazines are produced in high yields by dirhodium(II) carboxylate catalyzed reactions between nitrones and a β-TBSO-substituted vinyldiazoacetate. High enantiocontrol occurs with catalysis by N-phthaloyl-(S)-(amino acid)-ligated dirhodium carboxylates for [3 + 3]-cycloaddition reactions with both acyclic and cyclic nitrones.
摘要
通过金属卡宾与偶极子中间体的相互作用，在二价二钌羧酸酯催化下，硝酮与β-TBSO 取代的乙烯基重氮乙酸酯之间的反应可以高产率地生成 3,6-二氢-1,2-恶嗪。通过 N-邻苯二甲酰基-(S)-氨基酸配体的二钌羧酸酯催化，非环状和环状硝酮的[3+3]-环加成反应具有高对映选择性。
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