246232-25-7Relevant articles and documents
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 control
Soloshonok, Vadim A.,Cai, Chaozhong,Yamada, Takeshi,Ueki, Hisanori,Ohfune, Yasufumi,Hruby, Victor J.
, p. 15296 - 15303 (2005)
This paper describes a systematic study of addition reactions between the chiral Ni(II) complex of the Schiff base of glycine with (S)-o[N-(N- benzylprolyl)amino]benzophenone and (S)- or (R)-3-[(E)-enoyl]-4-phenyl-1,3- oxazolidin-2-ones as a general and s
A practical asymmetric synthesis of enantiomerically pure 3-substituted pyroglutamic acids and related compounds
Soloshonok, Vadim A.,Cai, Chaozhong,Hruby, Victor J.
, p. 2172 - 2175 (2000)
DBU-catalyzed Michael addition reactions were shown to occur at room temperature between a nickel(II) complex of the Schiff base of glycine 1 and (S)- or (R)-N-(E-enoyl)-4-phenyl-3-oxazolidin-2-ones (2, see scheme). This reaction, which has an almost comp
Michael addition reactions between various nucleophilic glycine equivalents and (S,E)-1-enoyl-5-oxo-N-phenylpyrrolidine-2-carboxamide, an optimal type of chiral Michael acceptor in the asymmetric synthesis of β-phenyl pyroglutamic acid and related compoun
Ellis, Trevor K.,Ueki, Hisanori,Tiwari, Rohit,Soloshonok, Vadim A.
scheme or table, p. 2629 - 2634 (2010/03/25)
(S)-5-Oxo-N-phenyl-1-[(E)-3-phenylacryloyl]pyrrolidine-2-carboxamide, easily prepared from inexpensive and readily available, in both enantiomeric forms, glutamic/pyroglutamic acid was designed as an optimal type of chiral Michael acceptor for reactions w
Virtually complete control of simple and face diastereoselectivity in the Michael addition reactions between achiral equivalents of a nucleophilic glycine and (S)- or (R)-3-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones: Practical method for preparation of β-substituted pyroglutamic acids and prolines
Soloshonok, Vadim A.,Ueki, Hisanori,Tiwari, Rohit,Cai, Chaozhong,Hruby, Victor J.
, p. 4984 - 4990 (2007/10/03)
This study demonstrates a new strategy for controlling the stereochemical outcome of the Michael addition reactions between nucleophilic glycine equivalents and α,β-unsaturated carboxylic acid derivatives: The addition reactions between achiral Ni(II)-complex of the Schiff base of glycine with o-[N-α-pycolylamino]acetophenone and (S)- or (R)-3-(E-enoyl)-4- phenyl-1,3-oxazolidin-2-ones were shown to occur at room temperature in the presence of nonchelating organic bases and, most notably, with very high stereoselectivity at both newly formed stereogenic centers. Thus, the chiral 4-phenyl-1,3-oxazolidin-2-one moiety was found to control efficiently both face diastereoselectivities of the glycine derived enolate and the C,C double bond of the Michael acceptor. The new strategy developed in this work is methodologically superior to previous methods, most notably in terms of generality and synthetic efficiency. Excellent chemical yields and diastereoselectivities, combined with the simplicity of the experimental procedures, render the present method of immediate use for preparing various 3-substituted pyroglutamic acids and related amino acids (glutamic acids, glutamines, prolines, etc.) available via conventional transformations of the former.
