Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, United States.
J Org Chem. 2021 Feb 19;86(4):3490-3534. doi: 10.1021/acs.joc.0c02899. Epub 2021 Feb 4.
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 to 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.
描述了一种通过有机金属试剂对丁基亚磺亚胺的加成反应作为关键步骤，以高产率和立体选择性实现高度取代的 1,2-氨基醇的不对称合成的一般方法。这些亚胺与有机锂试剂的加成遵循改进的 Davis 模型。此反应的立体选择性取决于亲核试剂和亲电试剂。这些高度取代的 1,2-氨基醇可用于以高产率合成立体化学多样且结构新颖的多取代 2,2'-亚甲基（双恶唑啉）配体。
