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Liu J, Li Y, Hu J. Stereoselective synthesis of di- and monofluoromethylated vicinal ethylenediamines with di- and monofluoromethyl sulfones. J Org Chem. 2007;72(8):3119-21doi: 10.1021/jo070094w.
Liu, J., Li, Y., & Hu, J. (2007). Stereoselective synthesis of di- and monofluoromethylated vicinal ethylenediamines with di- and monofluoromethyl sulfones. The Journal of organic chemistry, 72(8), 3119-21. https://doi.org/10.1021/jo070094w
Liu, Jun, et al. "Stereoselective synthesis of di- and monofluoromethylated vicinal ethylenediamines with di- and monofluoromethyl sulfones." The Journal of organic chemistry vol. 72,8 (2007): 3119-21. doi: https://doi.org/10.1021/jo070094w
Liu J, Li Y, Hu J. Stereoselective synthesis of di- and monofluoromethylated vicinal ethylenediamines with di- and monofluoromethyl sulfones. J Org Chem. 2007 Apr 13;72(8):3119-21. doi: 10.1021/jo070094w. Epub 2007 Mar 27. PMID: 17385922.
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J Org Chem. 2007 Apr 13;72(8):3119-21. doi: 10.1021/jo070094w. Epub 2007 Mar 27.

Stereoselective synthesis of di- and monofluoromethylated vicinal ethylenediamines with di- and monofluoromethyl sulfones.

The Journal of organic chemistry

Jun Liu, Ya Li, Jinbo Hu

Affiliations

  1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.

PMID: 17385922 DOI: 10.1021/jo070094w

Abstract

The diastereoselective nucleophilic (phenylsulfonyl)difluoromethylation and (phenylsulfonyl)monofluoromethylation of alpha-amino N-tert-butanesulfinimines (3) by using PhSO2CF2H and PhSO2CH2F reagents gave products 4 or 5 in high yields (73-99%) and with excellent diastereoselectivity (dr up to >99:1). After subsequent reductive desulfonylation and acid-catalyzed alcoholysis, compounds 4 and 5 could be readily transformed to chiral alpha-difluoromethylated or alpha-monofluoromethylated ethylenediamines in good yields.

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