Highly Diastereo- and Enantioselective Aza-Mannich Addition of Oxazolones to N-Boc Protected α-Amido Sulfones Catalyzed by Bifunctional Thiourea-modified Cinchona Alkaloid,ChemistrySelect

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Highly Diastereo- and Enantioselective Aza-Mannich Addition of Oxazolones to N-Boc Protected α-Amido Sulfones Catalyzed by Bifunctional Thiourea-modified Cinchona Alkaloid
ChemistrySelect ( IF 1.9 ) Pub Date : 2021-09-15 , DOI: 10.1002/slct.202102496
Hui Zhang _{1,

2} , Lihua Song ₁ , Weicheng Yuan ₃ , Xiaomei Zhang ₃

Affiliation

A diastereo- and enantioselective aza-Mannich addition of oxazolones to α-amino sulfones catalyzed by tertiary amine-1-phenylethyl thiourea based on cinchona structure has been developed. The reaction afforded the azlactone adducts bearing quaternary and tertiary stereogenic centers with high yields (up to 98 %) and moderate to excellent diastereo- and enantioselectivities (up to >99 : 1 dr and 96 % ee). The absolute configuration of a product was assigned by X-ray crystal structural analyses and a plausible reaction mechanism was proposed.

中文翻译：

双功能硫脲修饰的金鸡纳生物碱催化恶唑酮与 N-Boc 保护的 α-氨基砜的高度非对映选择性和对映选择性氮杂-曼尼希加成反应

基于金鸡纳结构的叔胺-1-苯乙基硫脲催化恶唑酮与α-氨基砜的非对映选择性和对映选择性氮杂-曼尼希加成反应已被开发。该反应以高产率（高达 98%）和中等至极好的非对映选择性和对映选择性（高达 >99:1 dr 和 96% ee）提供带有四级和三级立体中心的吖内酯加合物。通过 X 射线晶体结构分析确定了产物的绝对构型，并提出了合理的反应机制。

更新日期：2021-09-15

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