N‐Benzyl‐5‐hydroxy‐3‐pyrrolidin‐2‐one by Hydrogen Peroxide Oxidation of N‐Benzyl‐3‐phenylseleno‐2‐pyrrolidinone

References

• Ikota , N. and Hanaki , A. 1987 . Synthesis of (–)‐swainsonine and optically active 3,4‐dihydroxy‐2‐hydroxymethyl pyrrolidines . Chem. Pharm. Bull. , 35 : 2140 – 2370 .
   PubMed Web of Science ®Google Scholar
• Grieco , P. A. and Mujashita , M. 1974 . Organoselenium chemistry: α‐Phenylseleno lactones: New general route to the synthesis of fused α‐methylene lactones . J. Org. Chem. , 39 : 120 – 122 .
   Web of Science ®Google Scholar
• Mitchell , R. H. 1974 . Simple synthesis of trans‐alkenes from halides by selenoxide fragmentation . J. Chem. Soc., Chem. Commun. , : 990 – 991 .
   Google Scholar
• Sharpless , K. B. , Young , M. W. and Lauer , R. L. 1973 . Mild procedure for the conversion of epoxides to allylic alcohols: First organoselenium reagent . J. Am. Chem. Soc. , 95 : 2697 – 2699 .
   Web of Science ®Google Scholar
• Reich , H. J. , Renga , J. M. and Reich , I. L. 1974 . Organoselenium chemistry: conversion of cyclic ketones and α‐dicarbonyl compounds to enones . J. Org. Chem. , 39 : 2133 – 2135 .
   Google Scholar
• Sharpless , K. B. and Young , M. W. 1975 . Olefin synthesis: rate enhancement of the elimination of alkyl aryl selenoxides by electron‐withdrawing substituents . J. Org. Chem. , 40 : 947 – 949 .
   Web of Science ®Google Scholar
• Li , B. and Smith , M. B. 1995 . Preparation and epoxidation of conjugated lactams: Influence of ring size on epoxidation . Synth. Commun. , 25 : 1265 – 1275 .
   Web of Science ®Google Scholar
• Davis , D. A. and Gribble , G. 1990 . A regioselective Diels–Alder synthesis of ellipticine . Tetrahedron Lett. , 31 : 1081 – 1084 .
   Google Scholar
• Ohfune , Y. and Tomita , M. 1982 . Total synthesis of (–)‐domoic acid: A revision of the original structure . J. Am. Chem. Soc. , 104 : 3511 – 3513 .
   Web of Science ®Google Scholar
• Mun , J. and Smith , M. 2003 . B ORGN 376 . Paper presented at the 225th national meeting of the American Chemical Society . March 23 2003 , New Orleans, LA.
   Google Scholar
• Mase , N. , Nishi , T. , Hiyoshi , M. , Ichihara , K. , Bessho , J. , Yoda , H. and Takabe , K. 2002 . Regioselective reduction of maleimide and citraconimide derivatives: General preparation of 5‐hydroxy‐1,5‐dihydropyrrol‐2‐one . J. Chem. Soc., Perkin Trans. 1 , : 707 – 709 .
   Google Scholar
• Reddy , P. Y. , Kondo , S. , Toru , T. and Ueno , Y. 1997 . J. Org. Chem. , 62 : 2652 – 2657 .
   PubMed Web of Science ®Google Scholar
• Evans , D. A. and Andrews , G. C. 1974 . Allylic sulfoxides: Useful intermediates in organic synthesis . Acc. Chem. Res. , 7 : 147 – 155 .
   Web of Science ®Google Scholar
• Hoffmann , R. W. 1979 . Angew. Chem. Int. Ed. , 18 : 563 – 572 .
   Web of Science ®Google Scholar
• Reich , H. J. and Yelm , K. E. 1991 . Asymmetric induction in the oxidation of [2.2]paracyclophane‐substituted selenides: Application of chirality transfer in the selenoxide [2,3] sigmatropic rearrangement . J. Org. Chem. , 56 : 5672 – 5679 .
   Google Scholar
• Sharpless , K. B. and Lauer , R. F. 1972 . Selenium dioxide oxidation of olefins: Evidence for the intermediacy of allylseleninic acids . J. Am. Chem. Soc. , 94 : 7154 – 7155 .
   Web of Science ®Google Scholar
• Hori , T. and Sharpless , K. B. 1978 . Synthetic applications of arylselenenic and arylseleninic acids: Conversion of olefins to allylic alcohols and epoxides . J. Org. Chem. , 43 : 1689 – 1697 .
   Web of Science ®Google Scholar
• Trachtenberg , E. N. 1969 . Oxidation Edited by: Augustine , R. L. Vol. 1 , 119 – 187 . New York : Marcel‐Dekker .
   Google Scholar
• Waitkins , G. R. and Clark , C. W. 1945 . Selenium dioxide: Preparation, properties, and use as oxidizing agent . Chem. Rev. , 36 : 235 – 289 .
   Google Scholar
• Haines , A. H. 1985 . Methods for the Oxidation of Organic Compounds 25 London : Academic Press .
   Google Scholar