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铜(II)催化的不对称亨利反应,使用新型C1对称氨基蒎烷衍生配体。

Cu (II)-catalyzed asymmetric henry reaction with a novel C1-symmetric aminopinane-derived ligand.

作者信息

Filippova Liudmila, Stenstrøm Yngve, Hansen Trond Vidar

机构信息

Department of Chemistry, Biology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, N-1432 Ås, Norway.

Department of Pharmaceutical Chemistry, School of Pharmacy, University of Oslo, P.O. Box 1068, Blindern, N-0316 Oslo, Norway.

出版信息

Molecules. 2015 Apr 9;20(4):6224-36. doi: 10.3390/molecules20046224.

DOI:10.3390/molecules20046224
PMID:25859780
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6272271/
Abstract

A novel C1-symmetric dinitrogen ligand was synthesized in high yield from commercially available (1R,2R,3R,5S)-(-)-isopinocampheylamine and 1-methyl-2-imidazolecarboxaldehyde. In combination with Cu(OAc)2H2O, this new ligand promote the reaction between nitromethane and aliphatic aldehydes with high yields (up to 97%) and moderate enantioselectivities (up to 67% ee). The reactions with benzaldehyde required prolonged reaction time that resulted in diminished yields, but accompanied with ee-values in the 55%-76% range.

摘要

一种新型的C1对称二氮配体由市售的(1R,2R,3R,5S)-(-)-异松莰基胺和1-甲基-2-咪唑甲醛高产率合成。与Cu(OAc)₂·H₂O结合,这种新配体促进硝基甲烷与脂肪醛之间的反应,产率高(高达97%),对映选择性适中(高达67% ee)。与苯甲醛的反应需要延长反应时间,这导致产率降低,但对映体过量值在55%-76%范围内。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0315/6272271/e51e3eb2c574/molecules-20-06224-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0315/6272271/b76b7d268d01/molecules-20-06224-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0315/6272271/e51e3eb2c574/molecules-20-06224-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0315/6272271/b76b7d268d01/molecules-20-06224-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0315/6272271/e51e3eb2c574/molecules-20-06224-g002.jpg

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