Readily available new pyridyl alcohols derived from d-glucose as ligands for the enantioselective addition of diethylzinc to aldehydes

作者: Hanmin Huang , Zhuo Zheng , Huilin Chen , Changmin Bai , Junwei Wang

DOI: 10.1016/S0957-4166(03)00212-X

关键词:

摘要: Abstract A series of new chiral ligands derived from d -glucose has been synthesized and applied in the enantioselective addition diethylzinc to aldehydes. Up 94.1% e.e. was obtained ethylation reactions. In contrast -fructose, gave opposite asymmetric induction.

参考文章(31)
Suk-Ku Kang, Jae-Ho Jeon, Tokutaro Yamaguchi, Jae-Sun Kim, Byoung-Seob Ko, Enzymatic synthesis of (S)-(−)-1-(2-thienyl)propyl acetate Tetrahedron-asymmetry. ,vol. 6, pp. 2139- 2142 ,(1995) , 10.1016/0957-4166(95)00284-V
Jahyo Kang, Ha Young Kim, Joong Hyup Kim, Synthesis of chiral plane-extended pyridyl alcohols for the enantioselective addition of diethylzinc to aldehydes Tetrahedron-asymmetry. ,vol. 10, pp. 2523- 2533 ,(1999) , 10.1016/S0957-4166(99)00247-5
Emmanuel Macedo, Christina Moberg, Enantioselective addition of diethylzinc to aldehydes catalyzed by pyridineoxazolinealcohols Tetrahedron-asymmetry. ,vol. 6, pp. 549- 558 ,(1995) , 10.1016/0957-4166(95)00039-R
Yangjie Wu, Hongying Yun, Yusheng Wu, Kuiling Ding, Ying Zhou, Synthesis of N-α-pyridylmethyl amino alcohols and application in catalytic asymmetric addition of diethylzinc to aromatic aldehydes Tetrahedron-asymmetry. ,vol. 11, pp. 3543- 3552 ,(2000) , 10.1016/S0957-4166(00)00336-0
Miyuki Ishizaki, Ko-ichi Fujita, Mahoko Shimamoto, Osamu Hoshino, Catalysed asymmetric reaction of aldehydes with dialkylzinc in the presence of chiral pyridyl alcohols as ligands Tetrahedron: Asymmetry. ,vol. 5, pp. 411- 424 ,(1994) , 10.1016/S0957-4166(00)86213-8
E. J. Corey, Po Wai Yuen, Francis J. Hannon, Derk A. Wierda, Polyfunctional, structurally defined catalysts for the enantioselective addition of dialkylzinc reagents to aldehydes Journal of Organic Chemistry. ,vol. 55, pp. 784- 786 ,(1990) , 10.1021/JO00290A002
Huichang Zhang, Kin Shing Chan, Dramatic temperature effect in asymmetric catalysis in the enantioselective addition of diethylzinc to aldehydes Journal of The Chemical Society-perkin Transactions 1. pp. 381- 382 ,(1999) , 10.1039/A808920E