Absolute Configuration Determination of Azulenyl Diols Isolated From Asymmetric Pinacol Coupling.

作者: Eugenia Andreea Dragu , Jean-Valere Naubron , Anamaria Hanganu , Alexandru C. Razus , Simona Nica

DOI: 10.1002/CHIR.22523

关键词:

摘要: A convenient enantioselective approach for the pinacol coupling of 1-acetylazulene involving easily accessible (R)- or (S)-BINOLs as chiral additive is reported. This supposes preformation titanium-BINOL complex in 1:2 ratio and subsequent reduction with zinc when, 2,3-di(azulen-1-yl)butane-2,3-diol can be isolated around 60% enantiomeric excess. The absolute configuration enantiomers was assigned by comparison experimental Boltzmann-weighted calculated VCD ECD spectra (+)-(2S;3S)-di(azulen-1-yl)butane-2,3-diol. Chirality 27:826-834, 2015. © 2015 Wiley Periodicals, Inc.

参考文章(35)
Eugenia Andreea Dragu, Simona Nica, Victorita Tecuceanu, Daniela Bala, Constantin Mihailciuc, Anamaria Hanganu, Alexandru C. Razus, Synthesis and Electrochemical Properties of Carbocyclic and Heterocyclic Diazulenylethenes European Journal of Organic Chemistry. ,vol. 2013, pp. 6601- 6610 ,(2013) , 10.1002/EJOC.201300354
Takao Ikariya, A. John Blacker, Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts. Accounts of Chemical Research. ,vol. 40, pp. 1300- 1308 ,(2007) , 10.1021/AR700134Q
Philip J. Stephens, Frank J. Devlin, Jian-Jung Pan, The determination of the absolute configurations of chiral molecules using vibrational circular dichroism (VCD) spectroscopy Chirality. ,vol. 20, pp. 643- 663 ,(2008) , 10.1002/CHIR.20477
Saffet Celik, Murat Cakici, Hamdullah Kilic, Ertan Sahin, Synthesis of quinazolinone-based aziridine diols as chiral ligands: dual stereoselectivity in the asymmetric ethylation of aryl aldehydes Tetrahedron-asymmetry. ,vol. 26, pp. 152- 157 ,(2015) , 10.1016/J.TETASY.2014.12.011
Alexandru C. Razus, Eugenia Andreea Dragu, Simona Nica, Alina Nicolescu, Reductive coupling of (azulen-1-yl)carbonyl compounds by low-valent titanium; pinacol/pinacolone rearrangement versus pinacol and alkene generation Tetrahedron Letters. ,vol. 52, pp. 1858- 1862 ,(2011) , 10.1016/J.TETLET.2011.02.022
Jiwu Wen, Jun Zhao, Tianpa You, Asymmetric pinacol coupling catalyzed by TADDOL-titanium complexes Journal of Molecular Catalysis A-chemical. ,vol. 245, pp. 278- 280 ,(2006) , 10.1016/J.MOLCATA.2005.09.042
Ramesh N. Patel, Synthesis of chiral pharmaceutical intermediates by biocatalysis Coordination Chemistry Reviews. ,vol. 252, pp. 659- 701 ,(2008) , 10.1016/J.CCR.2007.10.031
Shunji Ito, Noboru Morita, Creation of Stabilized Electrochromic Materials by Taking Advantage of Azulene Skeletons European Journal of Organic Chemistry. ,vol. 2009, pp. 4567- 4579 ,(2009) , 10.1002/EJOC.200900393
Eugenia Andreea Dragu, Anamaria Hanganu, Ileana Rau, Francois Kajzar, Alexandrina Tane, Alexandru C. Razus, Simona Nica, Photochemistry of Fluorescent Azobenzenes Substituted with Azulenylpyridine Moiety Molecular Crystals and Liquid Crystals. ,vol. 604, pp. 41- 51 ,(2014) , 10.1080/15421406.2014.967653
John P. Perdew, Kieron Burke, Matthias Ernzerhof, Generalized Gradient Approximation Made Simple Physical Review Letters. ,vol. 77, pp. 3865- 3868 ,(1996) , 10.1103/PHYSREVLETT.77.3865