手性磺内酰胺双羟基衍生物的合成及晶体结构

SYNTHESIS AND CRYSTAL STRUCTURE OF DIHYDROXY DERIVATES WITH TRICYCLIC CHIRAL STULTAM

N 己烯酰基手性三环磺内酰胺经不对称双羟基化获得二醇 4和 5 ,再进一步转变为对应的二甲基缩酮 6和 7(6 7∶33) ,总产率 81%。经晶体结构分析 ,6的构型为 (Sc(10 ) ,Rc(11) ) ,C =O与SO2 为反式构型 ,其S(1) N(1) C(9) O(3)的二面角为 175 .91°。 7为 (Rc(10 ) ,Sc(11) ) ,C =O与SO2 为顺式构型 ,其对应二面角为 4.6

Asymmetric dihydroxylation of N-acryloyl tricyclic chiral stultam with RuCl\-3/NaIO\-4 Provided glycols 4/5. These diols were converted to the corresponding dimethyl acetals 6/7 in ratio 67:33 (total yield 81%). X-Ray crystallographic analyses confirmed that 6 with anti-disposed C=O and SO\-2 group has (S\-\{c(10)\}, R\-\{c(11)\}) configuration. It's dihedral angle of S(1)-N(1)-C(9)-O(3) is 175.91°; 7 with syn-disposed C=O and SO\-2 group exhibiting (R\-\{c(10)\}, S\-\{c(11)\}) configuration and dihedral angle 4.69°.