A new polymer-supported Evans-type chiral auxiliary derived from α-hydroxy-β-amino acid, phenylnorstatine: synthesis and application in solid-phase asymmetric alkylation reactions

A New Non‐Cross‐Linked Polystyrene Supported 2‐Phenylimino‐2‐oxazolidine Chiral Auxiliary: Synthesis and Application in Asymmetric Alkylation Reactions

“…[9,10] However, in most case, the expensive chiral auxiliaries could not be recovered after the reactions; to recycle these expensive materials, chiral auxiliaries have been supported onto polymers. [11][12][13][14][15] Insoluble polymer supports, such as, Merrifield resin and Wang resin, only require simple "filtration" to achieve rapidly the isolation of desired compounds or to recover expensive reagents or catalysts attached onto solid supports for recycling. [12,13] However, several shortcomings were shown because of nonlinear kinetic behavior, unequal distribution or access to the chemical reaction, and synthetic difficulties in transferring standard organic reactions to the solid phase.…”

“…[11][12][13][14][15] Insoluble polymer supports, such as, Merrifield resin and Wang resin, only require simple "filtration" to achieve rapidly the isolation of desired compounds or to recover expensive reagents or catalysts attached onto solid supports for recycling. [12,13] However, several shortcomings were shown because of nonlinear kinetic behavior, unequal distribution or access to the chemical reaction, and synthetic difficulties in transferring standard organic reactions to the solid phase. Soluble polymer supports, which combine the superiorities of insoluble polymer supports with the advantages of classic liquid synthesis, have been extensively studied by chemists.…”

Studies on the Synthesis and Dynamic NMR Properties of 2-(Benzylidene amino)-N-[(R)-2-hydroxy-2-methyl-1-phenylpropyl]acetamide

“…In this area, the use of enantiomerically pure oxazolidin-2-one derivatives as chiral auxiliaries in acyl group transformations, aldol reactions, conjugate addition, alkylation, azidation, hydroxylation, halogenation, amination and ȕ-lactam synthesis has been well demonstrated [2][3][4][5]. Currently, Davies et al have used SuperQuat 1 (Fig.…”

New Practical Synthesis of Non-Cross-Linked Polystyrene Supported 2-Phenylimino-2-Oxazolidine

“…4,5 However, it is difficult with some chiral auxiliaries to achieve a high degree of stereoselectivity in solid-supported reactions. 6 The soluble polymer supports, which combine the benefits of an insoluble polymer support with the advantages of classic liquid synthesis, have been extensively studied by chemists.…”

“…Insoluble polymer supports, such as the Merrifield resin and Wang resin provide a simple procedure involving "filtration" for rapidly achieving the isolation of desired compounds and recovering expensive reagents or catalysts attached to a solidsupport for recycling. 4,5 However, it is difficult with some chiral auxiliaries to achieve a high degree of stereoselectivity in solid-supported reactions. 6 The soluble polymer supports, which combine the benefits of an insoluble polymer support with the advantages of classic liquid synthesis, have been extensively studied by chemists.…”