Literature DB >> 29083001

The enantioselective addition of 1-fluoro-1-nitro(phenylsulfonyl)methane to isatin-derived ketimines.

M Urban1, M Franc1, M Hofmanová1, I Císařová2, J Veselý1.   

Abstract

An asymmetric organocatalytic addition of fluorinated phenylsulfonylnitromethane to isatin-derived ketimines was developed. The reaction was efficiently catalyzed by a chiral tertiary amine, cinchonine. This methodology provides a new type of optically active compound with two adjacent quaternary carbon stereocenters in good yield (up to 96%), with moderate diastereoselectivity (up to 5.7 : 1 dr) and excellent enantioselectivity (up to 98/96% ee).

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Year:  2017        PMID: 29083001     DOI: 10.1039/c7ob02408h

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  2 in total

Review 1.  Catalytic stereoselective Mannich-type reactions for construction of fluorinated compounds.

Authors:  Minoo Dabiri; Noushin Farajinia Lehi; Reza Mohammadian
Journal:  Mol Divers       Date:  2021-07-06       Impact factor: 2.943

2.  Fluorine-induced diastereodivergence discovered in an equally rare enantioselective syn-aza-Henry reaction.

Authors:  Jade A Bing; Nathan D Schley; Jeffrey N Johnston
Journal:  Chem Sci       Date:  2022-02-14       Impact factor: 9.825

  2 in total

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