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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 Jafari
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Dipti S. Kundu
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Pankaj Chauhan
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
V. P. Reddy Gajulapalli
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Carolina von Essen
b   Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland
,
Kari Rissanen
b   Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland
,
Dieter Enders*
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
› Author Affiliations
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Publication History

Received: 05 September 2017

Accepted: 12 September 2017

Publication Date:
04 October 2017 (online)

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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

Key words

asymmetric synthesis - isoxazole - trifluoromethyl ketone - squaramide organocatalyst - vinylogous Henry reaction

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590928.
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