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首页> 外文期刊>Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry >An expedient one-pot sequential three-component reaction for the stereoselective synthesis of functionalized spiro-sulfamidate inline fused δ-lactone scaffold
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An expedient one-pot sequential three-component reaction for the stereoselective synthesis of functionalized spiro-sulfamidate inline fused δ-lactone scaffold

机译：一种方便的一锅式顺序三组分反应，用于功能化螺氨基磺酰胺内联稠合δ-内酯支架的立体选择性合成

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摘要

A convenient one-pot three-component transformation between 4-aryl-5H-1,2,3-oxathiazole-2,2-diox-ides, trans-β-aryl/alkyl-substituted acroleins and paraformaldehyde in CH2Cl2 at room temperature in the presence of commercially available L-proline and DBU as the organocatalysts has been successfully realized for the first time via a Michael-condensation-hemiacetalization sequence process. The resulting functionalized spiro-sulfamidate imine fused δ-lactone scaffolds were obtained via in situ oxidation of spiro-5-lactols by PCC in good to excellent overall yields and moderate to good diastereomeric ratio (up to ≤5:1 dr). Moreover, a synthetically useful intermediate trans-cis-β-amino-α-azido compound has been successfully achieved through our procedure.
机译：在室温下于室温下于CH2Cl2中的4-芳基-5H-1,2,3-氧杂噻唑-2,2-二氧-化物，反式-β-芳基/烷基取代的丙烯醛和多聚甲醛之间进行便捷的一锅三组分转化商业上可得的L-脯氨酸和DBU作为有机催化剂的存在已首次通过迈克尔-缩合-半缩醛化顺序过程成功实现。所得功能化的螺-氨基磺酰胺基亚胺稠合的δ-内酯支架是通过PCC对螺-5-内酯进行原位氧化而获得的，其总收率良好至优异，非对映体比率中等至良好（最高≤5：1 dr）。此外，通过我们的方法已成功实现了合成上有用的中间体反式-顺式-β-氨基-α-叠氮基化合物。

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