Synthesis 2018; 50(02): 323-329
DOI: 10.1055/s-0036-1590928
paper
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Enantioselective Vinylogous Henry Reaction of 3,5-Dimethyl-4-nitroisoxazole with Trifluoromethyl Ketones

Ehsan Jafaria, Dipti S. Kundua, Pankaj Chauhana, V. P. Reddy Gajulapallia, Carolina von Essenb, Kari Rissanenb, Dieter Enders*a
  • aInstitute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
  • bDepartment of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland
Further Information

Publication History

Received: 05 September 2017

Accepted: 12 September 2017

Publication Date:
04 October 2017 (eFirst)

Abstract

The enantioselective vinylogous Henry reaction of 3,5-dimethyl-4-nitroisoxazole with trifluoromethyl ketones employing a bifunctional squaramide organocatalyst has been developed. A series of isoxazole bearing trifluoromethyl-substituted tertiary alcohols, 2-substituted (R)-1,1,1-trifluoro-3-(3-methyl-4-nitroisoxazol-5-yl)propan-2-ols, were obtained under these mild reaction conditions in good yields and moderate to good enantioselectivities

Supporting Information

 
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