A Unified Strategy for the Asymmetric Synthesis of Highly Substituted 1,2-Amino Alcohols Leading to Highly Substituted Bisoxazoline Ligands.
A Unified Strategy for the Asymmetric Synthesis of Highly Substituted 1,2-Amino Alcohols Leading to Highly Substituted Bisoxazoline Ligands.
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高度取代的 1,2-氨基醇的不对称合成导致高度取代的双恶唑啉配体的统一策略。
DOI：
10.1021/acs.joc.0c02899
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发表时间：
2021
期刊：
影响因子：
--
通讯作者：
Denmark,ScottE
中科院分区：
文献类型：
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作者：
Shrestha,Bijay;Rose,BrennanT;Olen,CaseyL;Roth,Aaron;Kwong,AdonC;Wang,Yang;Denmark,ScottE
本文介绍了一种高收率、非对构选择性高取代1,2-氨基醇的不对称合成方法，该方法以多种亲核试剂对叔丁基亚胺的有机金属加成为关键步骤。将有机锂试剂添加到这些亚胺中遵循改进的戴维斯模型。该反应的非对映选择性在很大程度上取决于亲核试剂和亲电试剂。这些高度取代的1,2-氨基醇被用于合成立体化学多样化和结构新颖的多取代2,2 ' -亚甲基（双恶唑啉）配体，收率高。
A general procedure for the asymmetric synthesis of highly substituted 1,2-amino alcohols in high yield and diastereoselectivity is described that uses organometallic additions of a wide range of nucleophiles totert-butylsulfinimines as the key step. The addition of organolithium reagents to these imines follows a modified Davis model. The diastereoselectivity for this reaction depends significantly on both the nucleophile and electrophile. These highly substituted 1,2-amino alcohols are used to synthesize stereochemically diverse and structurally novel, polysubstituted 2,2′-methylene(bisoxazoline) ligands in high yields.