手性哒嗪衍生物催化烯烃的不对称双羟化和氨羟化反应  

Asymmetic dihydroxylation and aminohydroxylation of olefins using 3,6-bis(9-O-quinidine)pyridazine

作　　者：王巧峰[1] 姜茹[1] 程司堃[1] 金瑛[1] 赵燕[1] 孙晓莉[1] 

机构地区：[1]第四军医大学药学系化学教研室,陕西西安710032

出　　处：《化学研究与应用》2007年第1期93-97,共5页Chemical Research and Application

基　　金：国家自然科学基金(20272082;20302014)资助项目;陕西省自然科学基金(2005B03)资助项目

摘　　要：A new ligand,3,6-bis（9-O-quinidine）pyridazine（（QD）2PYDZ）,was synthesized from quinidine and 3,6-dichloropyridazine under mild condition.It can be purified by recrystallization to give the yield of 73%.The use of（QD）2 PYDZ in asymmetric dihydroxylation（AD）of olelfins provided the corresponding chiral vicinal diols with 88～95%chemical yield and the values of enantiomeric excess（ess）are between 75% and 99%.Meanwhile,chiral β-amino alcohols with excellent eantioselectivity and regioselectivity were also achieved when the asymmetric aminohydroxylation（AA）of olefins were catalyzed by the complex（QD）2PYDZ-Os04.Their chemical yields ranged from 52%to 63%.In addition,during the AD reaction of ethyl trans-cinnamate,（QD）2PYDZ can be recovered and reused for five runs without any signilficant loss in its catalytlc efficiency.A new ligand, 3,6-his （ 9-O-quinidine ） pyridazine （ （ QD ） 2 PYDZ ）, was synthesized from quinidine and 3,6-diehloropyr- idazine under mild condition. It can be purified by recrystallization to give the yield of 73%. The use of（QD）2 PYDZ in asymmetric dihydroxylation（AD） of oleltlns provided the corresponding chiral vicinal diols with 88 - 95% chemical yield and the values of enantiomeric excess （ess） are between 75 % and 99 %. Meanwhile, chiral β-amino alcohols with excellent eantioselectivity and regioselec- tivity were also achieved when the asymmetric aminohydruxylation （AA）of olefins were catalyzed by the complex （QD）2PYDZ - Os04. Their chemical yields ranged from 52% to 63%. In addition,during the AD reaction of ethyl trans-einnamate, （QD）2PYDZ can be recovered and reused for five runs without any signililcant loss in its catalytic efficiency.

关 键 词：不对称双羟化 不对称氨羟化 手性连二醇 手性Β-氨基醇 3 6-双(9-O-奎尼丁)哒嗪 

分 类 号：O643[理学—物理化学]