Highly enantio selective addition of phenylacetylene to aldehydes catalyzed by titanium(IV) complexes of β-hydroxy amides

被引：19
作者：
Chen, Zhi-Ce
Hui, Xin-Ping [1 ]
Yin, Chao
Huang, Lu-Ning
Xu, Peng-Fei
Yu, Xiao-Xia
Cheng, Shao-Yi
机构：
[1] Chinese Acad Sci, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Jinchuan Grp Ltd, Gansu 737104, Peoples R China
来源：
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2007年 / 269卷 / 1-2期
基金：
中国国家自然科学基金;
关键词：
asymmetric addition; titanium tetraisopropoxide; phenylacetylene; diethylzinc; beta-hydroxy amide;
D O I：
10.1016/j.molcata.2007.01.025
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A series of chiral beta-hydroxy amide ligands was synthesized via the reaction of benzoyl chloride and chiral amino alcohols derived from L-amino acid. Titanium(IV) complexes of these new beta-hydroxy amide ligands were used for catalyzing the enantioselective addition of phenylacetylene to aldehydes. We found that the enantioselectivity of the reaction was strongly affected by the amount of titanium tetraisopropoxide and the solvent used. Chiral ligand 2b synthesized from 2-amino-3-ethyl-1-phenylpentan-3-ol was effective for the asymmetric alkynylation of aldehydes and the propargyl alcohols were obtained in high yields (up to 96%) and high enantiomeric excesses (up to 97%) under optimized conditions. A practical solution for preparing the chiral propargylic alcohol was described. (c) 2007 Elsevier B.V. All rights reserved.
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收藏
页码：179 / 182
页数：4
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