Chacko Shibin, Ramapanicker Ramesh
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, India 208016.
J Org Chem. 2015 May 1;80(9):4776-82. doi: 10.1021/acs.joc.5b00424. Epub 2015 Apr 17.
An efficient synthesis of deoxygalactonojirimycin and deoxyaltronojirimycin through the use of proline catalyzed asymmetric α-aminoxylation of a higher homologue of Garner's aldehyde, derived from l-aspartic acid, is reported. The method is also used for a highly diastereoselective synthesis of the N-Boc derivative of (2S,3S)-3-hydroxypipecolic acid. The configuration of the proline catalyst used for the asymmetric aminoxylation step ultimately controls the absolute configuration of three adjacent stereogenic centers in the final products.
报道了一种通过使用脯氨酸催化源自L-天冬氨酸的加纳醛的高级同系物的不对称α-氨基氧基化反应高效合成脱氧半乳糖野尻霉素和脱氧阿洛野尻霉素的方法。该方法还用于(2S,3S)-3-羟基哌啶酸的N-Boc衍生物的高度非对映选择性合成。用于不对称氨基氧基化步骤的脯氨酸催化剂的构型最终控制最终产物中三个相邻立体中心的绝对构型。
