多组分 Mannich 反应与重氮酯和 9-BBN 衍生的硼烯醇盐。
Multicomponent Mannich reactions with boron enolates derived from diazo esters and 9-BBN.
机构信息
Department of Chemistry, Center for Chemical Methodology and Library Development, Boston University, Boston, Massachusetts 02215, United States.
出版信息
Org Lett. 2011 May 6;13(9):2510-3. doi: 10.1021/ol200766t. Epub 2011 Apr 7.
Abstract
Diazo esters, arylboranes, and carbamoyl imines undergo a 3-component Mannich condensation reaction. Catalyzed by Cu(II) salts, the reaction affords the corresponding isocyanate Mannich product: one that can be easily trapped in situ by other nucleophiles. The Mannich condensation corresponds to an α,α-disubstituted enolate addition to imines. The reaction was rendered asymmetric by using the (-)-phenylmenthol ester in good yield and selectivities.
摘要
重氮酯、芳基硼烷和碳酰胺亚胺经历了 3 组分的曼尼希缩合反应。在 Cu(II)盐的催化下，反应得到相应的异氰酸酯曼尼希产物：一种可以很容易地被其他亲核试剂就地捕获的产物。曼尼希缩合反应对应于α,α-二取代烯醇化物对亚胺的加成。使用（-）-苯甲托酯以良好的产率和选择性实现了不对称反应。
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