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Asymmetric Reduction of tert-Butanesulfinyl Ketimines by N-Heterocyclic Carbene Boranes

Tao Liu, Ling-yan Chen and Zhihua Sun*

*College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai, China, Email: sungarisgmail.com

T. Liu, L-y. Chen, Z. Sun, J. Org. Chem., 2015, 80, 11441-11446.

DOI: 10.1021/acs.joc.5b02084 (free Supporting Information)


Abstract

A triazole-based N-heterocyclic carbene borane (NHC-borane) enables an efficient and highly diastereoselective reduction of various of tert-butanesulfinyl ketimines. The reagent was more efficient than or comparable to commonly used reductive reagents such as NaBH4, NaBH3CN, l-selectride, a Ru catalyst, or BH3-THF.

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Key Words

reduction of imines, boranes


ID: J42-Y2015