碘化钐介导的 Reformatsky 反应在立体选择性制备β-羟基-γ-氨基酸中的应用：异丝氨酸和 Dolaisoleucine 的合成。
Samarium iodide-mediated Reformatsky reactions for the stereoselective preparation of β-hydroxy-γ-amino acids: synthesis of isostatine and dolaisoleucine.
机构信息
Chemical Biology Laboratory, Molecular Discovery Program, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Frederick, Maryland 21702, United States.
出版信息
J Org Chem. 2012 Jan 6;77(1):733-8. doi: 10.1021/jo202091r. Epub 2011 Dec 14.
Abstract
The synthesis of β-hydroxy-γ-amino acids via SmI(2)-mediated Reformatsky reactions of α-chloroacetyloxazolidinones with aminoaldehydes is reported. Diastereoselective coupling is demonstrated to depend on the absolute configuration of the Evans chiral auxiliary employed in the reaction, allowing erythro or threo products to be obtained selectively. The potential utility of the methodology is exemplified by the facile synthesis of biologically relevant N-Boc-isostatine (2b) and N-Boc-dolaisoleucine (3c).
摘要
通过 SmI(2)-介导的α-氯乙酰基恶唑烷酮与氨基酸醛的 Reformatsky 反应合成了β-羟基-γ-氨基酸。研究表明，非对映选择性偶联取决于反应中所使用的 Evans 手性助剂的绝对构型，可以选择性地得到赤型或苏型产物。该方法的潜在用途通过生物相关的 N-Boc-异亮氨酸（2b）和 N-Boc-别亮氨酸（3c）的简便合成得到了例证。
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