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2002.9 - 2006.6 Nankai University, College of Chemistry, B. S.
2006.9 - 2009.7 Nankai University, SKLEOC, M. S.
2010.6 - Now University of California, Santa Barbara
Optically active b-aryloxyalcohols is one of the most important building blocks for the preparation of various pharmaceutical compounds and nature products. The existed asymmetric approaches to these chiral alcohols are rare. Thus, development of high efficient chiral b-aryloxyalcohols synthesis methods, such as asymmetric hydrogenation of racemic a-aryloxy ketones via dynamic kenitic resolution (DKR), is highly desirable and a challange task.
In this thesis, a high efficient Ru(II)-SDPs/diamines catalyzed asymmetric hydrogenation of the racemic a-aryloxy ketones via DKR has been developed. Up to 99.1% ee and > 99:1 cis- or anti-selectivities were obtained for a series of b-aryloxyalcohols. And this high efficient method has been successfully applied in the synthesis of a potent anti-inflammatory chiral drug 15.
In this study, we obtained 4 single crystals suitable for X-ray diffraction test for determining the configuration of the b-aryloxyalcohols. 52 compounds were synthesized, which included 7 new compounds. All of these compounds were identified by 1H NMR. All of these new compounds were identified by 1H NMR, 13C NMR and HRMS analysis. Keywords:a-aryloxy ketones, b-aryloxyalcohols, catalytic asymmetric hydrogenation, dynamic kinetic resolution (DKR), Ru(II)-SDPs/diamine catalyst
Keywords:a-aryloxy ketones, b-aryloxyalcohols, catalytic asymmetric hydrogenation, dynamic kinetic resolution (DKR), Ru(II)-SDPs/diamine catalyst
1. Wen-Ju Bai, Jian-Hua Xie, Ya-Li Li, Sheng Liu, Qi-Lin Zhou*, Enantioselective synthesis of chiral β-aryloxyalcohols by ruthenium- catalyzed ketone hydrogenation via DKR, Adv. Synth. Catal. 2010, 352, 81-84.
2.Jian-Hua Xie, Wei-Ling Kong, Xiao-Cheng Wang, Wen-Ju Bai, Li-Xin Wang, Qi-Lin Zhou*, Chiral ruthenium-SDPs/diamine complexes-catalyzed enantioselective hydrogenation of α-alkyl arylacetones via dynamic kinetic resolution, Front. Chem. China 2009, 4, 299-306.
3.Jian-Hua Xie, Sheng Liu, Wei-Ling Kong, Wen-Jun Bai, Xiao-Chen Wang, Li-Xin Wang, Qi-Lin Zhou*, Highly enantioselective and diastereoslective synthesis of chiral amino alcohols by ruthenium-catalyzed asymmetric hydrogenation of α-amino aliphatic ketones, J. Am. Chem. Soc. 2009, 131, 4222-4223.