Diastereoselective Mannich reactions of pseudo-C2-symmetric glutarimide with activated imines

Tatsuya Ishikawa; Tomoko Kawasaki-Takasuka; Toshio Kubota; Takashi Yamazaki

doi:10.3762/bjoc.13.244

Beilstein Journal of Organic Chemistry (Nov 2017)

Diastereoselective Mannich reactions of pseudo-C2-symmetric glutarimide with activated imines

Tatsuya Ishikawa,
Tomoko Kawasaki-Takasuka,
Toshio Kubota,
Takashi Yamazaki

Affiliations

Tatsuya Ishikawa: Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei 184-8588, Japan
Tomoko Kawasaki-Takasuka: Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei 184-8588, Japan
Toshio Kubota: Department of Biomolecular Functional Engineering, Ibaraki University, Nakanarusawa 4-12-1, Hitachi 316-8511, Japan
Takashi Yamazaki: Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei 184-8588, Japan

DOI: https://doi.org/10.3762/bjoc.13.244
Journal volume & issue: Vol. 13, no. 1
pp. 2473 – 2477

Abstract

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As an extension of the boron enolate-based aldol reactions, the oxazolidinone-installed bisimide 1a from 3-(trifluoromethyl)glutaric acid was employed for Mannich reactions with tosylated imines 2 as electrophiles to successfully obtain the corresponding adducts in a stereoselective manner.

Published in Beilstein Journal of Organic Chemistry

ISSN: 1860-5397 (Online)
Publisher: Beilstein-Institut
Country of publisher: Germany
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.beilstein-journals.org/bjoc

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