PMID: 11312965Apr 21, 2001Paper

Michael addition reactions between chiral Ni(II) complex of glycine and 3-(trans-enoyl)oxazolidin-2-ones. A case of electron donor-acceptor attractive interaction-controlled face diastereoselectivity

The Journal of Organic Chemistry
Chaozhong CaiVictor J Hruby

Abstract

This study has demonstrated that the readily available and inexpensive 3-(trans-3'-alkyl/arylpropenoyl)oxazolidin-2-ones, featuring high electrophilicity and conformational homogeneity, are synthetically superior Michael acceptors over the conventionally used alkyl enoylates, allowing for a remarkable improvement in reactivity and, in most cases, diastereoselectivity of the addition reactions with a Ni(II) complex of the chiral Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone. Kinetically controlled diastereoselectivity in the corresponding Michael addition reactions between the Ni(II) complex of glycine and the oxazolidin-2-ones was systematically studied as a function of steric, electronic, and position effects of the substituents on the starting Michael acceptor. In both aliphatic and aromatic series the simple diastereoselectivity was found to be virtually complete, affording the products via the corresponding TSs with the approach geometry like. The face diastereoselectivity of the reactions between the Ni(II) complex of glycine and the 3-(trans-3'-alkylpropenoyl)oxazolidin-2-ones was found to depend exclusively on the steric bulk of the alkyl group on the starting Michael acceptor. In contrast, the ...Continue Reading

Citations

Feb 5, 2011·The Journal of Organic Chemistry·Daniel J SmithJoel P Schneider
Dec 17, 2009·The Journal of Organic Chemistry·Victor J Hruby
Jun 25, 2009·Chemical Society Reviews·Julien MichauxJean-Marc Campagne
Aug 1, 2009·Future Medicinal Chemistry·Vadim A SoloshonokYasufumi Ohfune
Aug 1, 2009·Future Medicinal Chemistry·Valery P KukharVadim A Soloshonok
Jun 28, 2018·Organic & Biomolecular Chemistry·Ryosuke TakedaVadim A Soloshonok
Jul 21, 2005·Organic & Biomolecular Chemistry·Emilie L BentzSusan M Westaway
Jun 18, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yupiao ZouVadim A Soloshonok
Aug 10, 2017·Organic & Biomolecular Chemistry·Ryosuke TakedaVadim A Soloshonok
Nov 20, 2019·European Journal of Medicinal Chemistry·Haibo MeiVadim A Soloshonok
May 9, 2009·Journal of the American Chemical Society·Vadim A SoloshonokTaizo Ono
Aug 23, 2019·Chemical Reviews·Johann MoschnerBeate Koksch
Aug 30, 2018·The Journal of Organic Chemistry·Linda TaHenrik Sundén

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