Highly Enantioselective α-aminoxylation Reactions Catalyzed by Isosteviol-proline Conjugates in Buffered Aqueous Media

Authors: An, Ya-Jie¹; Wang, Chuan-Chuan¹; Xu, Yuan-Zhen¹; Wang, Wei-Juan¹; Tao, Jing-Chao²

Source: Catalysis Letters, Volume 141, Number 8, August 2011 , pp. 1123-1129(7)

Publisher: Springer

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Abstract:

Chiral amphiphilic conjugate catalysts were designed and synthesized by covalently connecting l-proline with an inexpensive natural product, isosteviol. These catalysts demonstrated remarkable efficiency in the asymmetric α-aminoxylation of aldehydes and ketones using nitrosobenzene in phosphate buffer solution, resulting in good to high yields and excellent enantioselectivities without using any additives. At pH 9.1, the amphiphilic catalysts showed a pH responsive ability in phosphate buffer solution, which facilitated the excellent O-selectivity reactions, illustrating a viable approach for the development of asymmetric supra-molecular catalysts.

Keywords: Amphiphilic conjugate; Aminoxylation; Buffered media; pH responsibility

Document Type: Research article

DOI: http://dx.doi.org/10.1007/s10562-011-0574-6

Affiliations: 1: Department of Chemistry, New Drug Research and Development Center, Zhengzhou University, 450052, Zhengzhou, People's Republic of China 2: Department of Chemistry, New Drug Research and Development Center, Zhengzhou University, 450052, Zhengzhou, People's Republic of China, Email: jctao@zzu.edu.cn

Publication date: 2011-08-01