节点文献
N-烃基化和N-磺酰化的手性氨基醇和硼烷对前手性酮的不对称还原
Asymmetric Reduction of Prochiral Ketones by Borane Catalyzed by N-Alkylated and N-Sulfonylated Chiral Aminoalcohol
【摘要】 为研究不对称催化合成反应,以L 亮氨酸为原料,由酯化、格式反应、还原N 烃基化反应合成3个新手性胺醇(6a,6b,6c),6b和6c经磺酰化得7a和7b.将手性配体6a,6b,6c,7a,7b分别与BH3·Me2S络合,由2种方法对芳香酮进行不对称还原,得芳香醇,不对称还原收率(ee)为3.9%~60.5%,其中手性磺胺醇的不对称催化收率较胺醇高.
【Abstract】 Asymmetric synthesis is becoming an even more interesting research area in chemistry.Aminoalcohols 6a, 6b and 6c were synthesized from L-leucine via esterification, Grignard reaction and reductive N-alkylation. Tosylation of 6b and 6c yielded 7a and 7b. After complexing with BH3·Me2S, 6a, 6b, 6c, 7a and 7b were tested in asymmetric reduction of aromatic ketones,to yield aromatic alcohols. The ee values ranged from (3.9%) to 60.5%. Tosylated ligands 7a and 7b gave better result than 6b and 6c.
【关键词】 不对称合成;
N烃基化;
N磺酰化;
硼烷;
胺基醇;
【Key words】 asymmetric synthesis; N-alkylation; N-sulfonylation; borane; aminoalcohol;
【Key words】 asymmetric synthesis; N-alkylation; N-sulfonylation; borane; aminoalcohol;
【基金】 天津大学青年教师基金资助项目(W50501).
- 【文献出处】 天津大学学报 ,Journal of Tianjin University , 编辑部邮箱 ,2004年10期
- 【分类号】O621.254.2
- 【被引频次】1
- 【下载频次】244