Functionalised pyrrolidinones derived from (S)-pyroglutamic acid

Diastereospecific synthesis of (S,S)‐2‐substituted‐4,4‐diphenyl‐3, 1‐oxazabicyclo[3.3.0]octanes

“…They also occur in a variety of natural products and pharmaceutically active compounds, either as isolated ring systems or embedded in more complex structures, which often possess wide rang- ing biological activity [1]. The development of the methodology for the preparation of highly functionalized pyrrolidines has attracted considerable interest recently [1][2][3][4]. The trans bicyclic derivatives of pyrrolidine, trans-3,1-oxazabicyclo [3.3.0]octan-8-one derivatives, can be synthesized mainly from aldehydes and related chiral hydroxymethylpyrrolidinones, which are derived from L-pyroglutamic acid [1][2][3][4]13].…”

“…The development of the methodology for the preparation of highly functionalized pyrrolidines has attracted considerable interest recently [1][2][3][4]. The trans bicyclic derivatives of pyrrolidine, trans-3,1-oxazabicyclo [3.3.0]octan-8-one derivatives, can be synthesized mainly from aldehydes and related chiral hydroxymethylpyrrolidinones, which are derived from L-pyroglutamic acid [1][2][3][4]13]. Herein we report the preparation of cis bicyclic derivatives of pyrrolidine, chiral cis-3,1-oxazabicyclo[3.3.0]octanes, from aldehydes and (S)-2-(hydroxydiphenylmethyl)pyrrolidine, which was obtained from L-proline.…”

“…Functionalized pyrrolidines are compounds of considerable importance since they are a source of useful synthetic intermediates [5][6][7], chiral auxiliaries [8,9], and ligands [10][11][12]. They also occur in a variety of natural products and pharmaceutically active compounds, either as isolated ring systems or embedded in more complex structures, which often possess wide rang- ing biological activity [1]. The development of the methodology for the preparation of highly functionalized pyrrolidines has attracted considerable interest recently [1][2][3][4].…”

“…During the last decade, pyroglutamic acid, the cyclized form of glutamic acid, has been widely studied for the synthesis of pyrrolidine derivatives [1][2][3][4]. Functionalized pyrrolidines are compounds of considerable importance since they are a source of useful synthetic intermediates [5][6][7], chiral auxiliaries [8,9], and ligands [10][11][12].…”

Stereoselective Hydrogenation ofCCBonds: Application to Drug and Natural Product Synthesis

“…157,158 A number of synthetic approaches [159][160][161][162] to aliskiren have been patented [163][164][165][166][167] by Novartis and Speedel Pharma (Basel, Switzerland) or published in a number of original articles. [168][169][170][171][172][173] Synthetic strategies 174 are often based on visual imaging of a target structure. 175 For several aliskiren syntheses, a highly enantioselective hydrogenation of a selected substrate has been chosen to insert a chiral center.…”