Journal ArticleDOI
One-pot, large-scale synthesis of Nickel(II) complexes derived from 2-[N-(alpha-picolyl)amino]benzophenone (PABP) and alpha- or beta-amino acids.
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TLDR
A one-pot, large-scale procedure for preparing the Belokon-Soloshonok nucleophilic glycine equivalent 2-[N-(alpha-picolyl)amino]benzophenone (PABP) derived Ni(II) complex [GlyNi( II)PABP] is described.Abstract:
A one-pot, large-scale procedure for preparing the Belokon-Soloshonok nucleophilic glycine equivalent 2-[N-(alpha-picolyl)amino]benzophenone (PABP) derived Ni(II) complex [GlyNi(II)PABP] is described. It has been accomplished by using isobutyl chloroformate to form PABP and then NaH/KOH as mixed bases to afford the corresponding complexes in a one-pot manner (up to an overall yield of 98%). The potential of this method for preparation of beta-amino acids derivatives, such as beta-AlaNi(II)PABP and beta-PheNi(II)PABP, has been demonstrated. The structure of beta-AlaNi(II)PABP is characterized by single-crystal X-ray diffraction.read more
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Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases; Part 1: alkyl halide alkylations
Alexander E. Sorochinsky,Jose Luis Acena,Hiroki Moriwaki,Tatsunori Sato,Vadim A. Soloshonok,Vadim A. Soloshonok +5 more
TL;DR: Straightforward, easy preparation as well as high reactivity of these Ni(II) complexes render them ready available and inexpensive glycine equivalents for preparing a wide variety of α-amino acids, in particular on a relatively large scale.
Journal ArticleDOI
Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 3: Michael addition reactions and miscellaneous transformations
Jose Luis Acena,Alexander E. Sorochinsky,Alexander E. Sorochinsky,Alexander E. Sorochinsky,Vadim A. Soloshonok,Vadim A. Soloshonok +5 more
TL;DR: A chiral auxiliary can be used as a part of nucleophilic glycine Ni(II) complex, Michael acceptor or both, leading to the conditions of matching vs. mismatching stereochemical preferences.
Journal ArticleDOI
Synthesis of fluorine-containing α-amino acids in enantiomerically pure form via homologation of Ni(II) complexes of glycine and alanine Schiff bases
Jose Luis Acena,Alexander E. Sorochinsky,Alexander E. Sorochinsky,Alexander E. Sorochinsky,Hiroki Moriwaki,Tatsunori Sato,Vadim A. Soloshonok,Vadim A. Soloshonok +7 more
TL;DR: In this article, a comprehensive treatment of literature data dealing with asymmetric synthesis of FAAs via homologation of chiral and achiral Ni(II) complexes of glycine and alanine Schiff bases using fluorinated electrophilic reagents is provided.
Journal ArticleDOI
Asymmetric Synthesis of Sterically and Electronically Demanding Linear ω-Trifluoromethyl Containing Amino Acids via Alkylation of Chiral Equivalents of Nucleophilic Glycine and Alanine
TL;DR: An operationally convenient, scalable asymmetric synthesis of linear, ω-trifluoromethyl-containing amino acids, which were not previously produced in their enantiomerically pure form, has been developed via alkylation of chiral equivalents of nucleophilic glycine and alanine.
Journal ArticleDOI
Highly diastereo- and enantioselective synthesis of syn-β-substituted tryptophans via asymmetric Michael addition of a chiral equivalent of nucleophilic glycine and sulfonylindoles
TL;DR: The asymmetric synthesis of syn-β-substituted tryptophan derivatives was carried out by the Michael addition of chiral equivalent of nucleophilic glycine with sulfonylindoles, and high diastereo- and enantioselectivities were achieved.
References
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Journal ArticleDOI
Synthesis and characterization of a metallabenzyne
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Synthesis of α-Amino Acids via Asymmetric Phase Transfer-Catalyzed Alkylation of Achiral Nickel(II) Complexes of Glycine-Derived Schiff Bases
Yuri N. Belokon,Natalia B. Bespalova,Tatiana D. Churkina,Ivana Císařová,Marina G. Ezernitskaya,Syuzanna R. Harutyunyan,Radim Hrdina,Henri B. Kagan,Pavel Kočovský,Konstantin A. Kochetkov,Oleg V. Larionov,Konstantin A. Lyssenko,Michael North,Miroslav Polášek,Alexander S. Peregudov,Vladimir V. Prisyazhnyuk,Štěpán Vyskočil +16 more
TL;DR: An unusually large positive nonlinear effect was observed in these reactions, and implications of the association and self-association of NOBIN for the observed sense of asymmetric induction and nonlinear effects are discussed.
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Michael addition reactions between chiral equivalents of a nucleophilic glycine and (S)- or (R)-3-[(E)-enoyl]-4-phenyl-1,3-oxazolidin-2-ones as a general method for efficient preparation of β-substituted pyroglutamic acids. Case of topographically controlled stereoselectivity
Vadim A. Soloshonok,Chaozhong Cai,Takeshi Yamada,Hisanori Ueki,Yasufumi Ohfune,Victor J. Hruby +5 more
TL;DR: Excellent chemical and stereochemical yields are rendered, combined with the simplicity and operational convenience of the experimental procedures, render the present method of immediate use for preparing various beta-substituted pyroglutamic acids and related compounds.
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Highly Efficient Catalytic Synthesis of α-Amino Acids under Phase-Transfer Conditions with a Novel Catalyst/Substrate Pair
Yuri N. Belokon,Konstantin A. Kochetkov,Tatiana D. Churkina,N. S. Ikonnikov,Oleg V. Larionov,Syuzanna R. Harutyunyan,Stepan Vyskocil,Michael North,Henri B. Kagan +8 more
TL;DR: In this article, a facile and fast enantioselective synthesis of α-amino acids with high ee values was achieved by the asymmetric alkylation of the glycine derivative under phase-transfer conditions with either (R)- or (S)-2amino-2'-hydroxy-1,1'-binaphthyl (NOBIN).
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(S)- or (R)-3-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones: Ideal Michael acceptors to afford a virtually complete control of simple and face diastereoselectivity in addition reactions with glycine derivatives
TL;DR: Enantiomerically pure (S)- or (R)-3-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones were found to serve as ideal Michael acceptors in addition reactions with achiral Ni(II) complexes of glycine Schiff bases.