Ko Soo Y
Department of Chemistry and Division of Molecular and Life Sciences, Ewha Womans University, Seoul 120-750, Korea.
J Org Chem. 2002 Apr 19;67(8):2689-91. doi: 10.1021/jo015967f.
Mitsunobu reactions of syn-2,3-dihydroxy esters exhibit a complete regioselection for the beta-hydroxyl group. Benzoylation, azidation, and tosylation have been performed under these conditions. Beta-functionalizations of syn-2,3-dihydroxy esters are uncommon, and the Mitsunobu reactions are complementary to other diol chemistries in the regioselection. In addition, the configurational inversion accompanying the Mitsunobu protocol offers a means for diastereochemical diversity, as exemplified by a synthesis of statine and its anti diastereomer. These findings will further expand the synthetic utilities of the Sharpless AD process.
顺式-2,3-二羟基酯的 Mitsunobu 反应对β-羟基表现出完全的区域选择性。在这些条件下已进行了苯甲酰化、叠氮化和甲苯磺酰化反应。顺式-2,3-二羟基酯的β-官能化并不常见，并且 Mitsunobu 反应在区域选择性方面与其他二醇化学方法互为补充。此外，Mitsunobu 反应过程中伴随的构型翻转提供了一种实现非对映化学多样性的方法，以他汀及其非对映异构体的合成为例。这些发现将进一步扩展 Sharpless 不对称双羟基化反应的合成应用。
