Direct catalytic enantioselective mannich reactions:: Synthesis of protected anti-α,β-diamino acids
Direct catalytic enantioselective mannich reactions:: Synthesis of protected anti-α,β-diamino acids
复制标题
DOI：
10.1021/ja073473f
复制
发表时间：
2007-09-05
影响因子：
15
通讯作者：
Willis, Michael C.
中科院分区：
文献类型：
--
作者：
Cutting, Gary A.;Stainforth, Nikki E.;Willis, Michael C.
使用直接催化对映选择性曼尼希反应制备反构型受保护 α,β 二氨基酸，其 ee 高达 99%。包含手性双（恶唑啉）配体、Mg(ClO4)(2) 和 HOnigs 碱的催化剂体系可促进异硫氰酸酯取代的酰亚胺加成到各种芳基、杂芳基、烯基和烷基衍生的亚胺上。将产物转化为其异丙酯衍生物允许差向异构化为顺式非对映体。
Anti-configured protected alpha,beta diamino acids are prepared with up to 99% ee using a direct catalytic enantioselective Mannich reaction. A catalyst system incorporating a chiral bis (oxazoline) ligand, Mg(ClO4)(2) and HOnigs base, promotes the addition of an isothiocyanate-substituted imide to a variety of aryl-, heteroaryl-, alkenyl-, and alkyl-derived imines. Conversion of the products to their i Pr-ester derivatives allows epimerization to the syn -diastereomers.