Di Bussolo Valeria, Caselli Micaela, Romano Maria Rosaria, Pineschi Mauro, Crotti Paolo
Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy.
J Org Chem. 2004 Dec 10;69(25):8702-8. doi: 10.1021/jo048981b.
6-O-Trityl- (1a) and 6-(O-benzyl)-substituted epoxide (1b) derived from D-glucal were examined in their addition reactions with O-, C-, N-, and S-nucleophiles. A 1,4-regio- and beta-stereoselective or an anti 1,2-addition pathway is commonly observed depending on the ability of the nucleophile to coordinate with the oxirane oxygen. When TMSN(3) or LiN(3) are used as azide-based nucleophiles, a 1,2-syn-addition pathway is also observed.
研究了由D-葡糖烯衍生的6-O-三苯甲基-（1a）和6-（O-苄基）取代的环氧化物（1b）与O-、C-、N-和S-亲核试剂的加成反应。根据亲核试剂与环氧乙烷氧配位的能力，通常会观察到1,4-区域和β-立体选择性或反式1,2-加成途径。当使用TMSN(3)或LiN(3)作为基于叠氮化物的亲核试剂时，也会观察到1,2-顺式加成途径。
