Brailsford John A, Zhu Liang, Loo Mandy, Shea Kenneth J
Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, CA 92697-2025, USA.
J Org Chem. 2007 Nov 23;72(24):9402-5. doi: 10.1021/jo701964b. Epub 2007 Nov 1.
The type 2 intramolecular Diels-Alder (IMDA) reaction is a valuable method for synthesis of both carbocyclic and heterocyclic bridged bicyclo[5.3.1]undecane and bicyclo[4.3.1]decane ring systems. These structures are common to a number of biologically important natural products. Asymmetric variants of the type 2 IMDA reaction incorporating oxazolidinone chiral auxiliaries have been evaluated. This study has resulted in systems that deliver bridged bicyclic [5.3.1] and [4.3.1] ring systems in high diastereomeric (97-99% de) and enantiomeric purity.
2型分子内狄尔斯-阿尔德（IMDA）反应是合成碳环和杂环桥连双环[5.3.1]十一烷和双环[4.3.1]癸烷环系的一种有价值的方法。这些结构在许多具有生物学重要性的天然产物中很常见。已对包含恶唑烷酮手性助剂的2型IMDA反应的不对称变体进行了评估。这项研究已得到能以高非对映体纯度（97-99% de）和对映体纯度提供桥连双环[5.3.1]和[4.3.1]环系的体系。
