Synthesis of 4‐(R)‐Naphthalene‐2‐yloxy‐1‐(1‐Phenyl‐(S)‐Ethyl)‐Pyrrolidin‐3‐(R)‐ol and 4‐(S)‐Naphthalen‐2‐yloxy‐1‐(1‐Phenyl‐(S)‐Ethyl)‐Pyrrolidin‐3‐(S)‐ol: Versatile Chiral Intermediates for Synthesis

References

• Numata , A. and Ibrika , T. 1987 . The Alkaloids Edited by: Brossi , A. Vol. 31 , New York : Academic Press . Chap. 6
   Google Scholar
• Denmark , S. E. and Marcin , L. R. 1995 . Asymmetric nitroalkene [4+2] cycloadditions: Enantioselective synthesis of 3‐substituted and 3,4‐disubstituted pyrrolidines . J. Org. Chem. , 60 : 3221 – 3235 .
   Google Scholar
• Bachi , M. D. , Bar‐Ner , N. and Melman , A. 1996 . Stereoselctive synthesis of (±)‐α‐kainic acid using free radical key reactions . J. Org. Chem. , 61 : 7116 – 7124 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMedGoogle Scholar
• Ibnusaud , I. and Thomas , G. 2003 . Biologically interesting chiral 3,4‐disubstituted pyrrolidines from optically active hydroxycitric acid lactones . Tetrahedron Lett. , 44 : 1247 – 1249 . [CROSSREF]
   Google Scholar
• Willoughby , C. A. , Rosauer , K. G. , Hale , J. L. , Budhu , R. J. , Mills , S. G. , Chapman , K. T. , MacCoss , M. , Malkowitz , L. , Springer , M. S. , Gould , S. L. , DeMartino , J. A. , Siciliano , S. J. , Cascieri , M. A. , Carella , A. , Carver , G. , Holmes , K. , Schleif , W. A. , Danzeisen , R. , Hazuda , D. , Kessler , J. , Lineberger , J. , Miller , M. and Emini , E. A. 2003 . 1,3,4‐trisubstituted pyrrolidine CCR5 receptor antagonists bearing 4‐aminoheterocycle substituted piperidine side chains . BioOrganic Med. Chem. Lett. , 13 : 427 – 431 . [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Lynch , C. L. , Hale , J. J. , Budhu , R. J. , Gentry , A. L. , Finke , P. E. , Caldwell , C. G. , Mills , S. G. , MacCross , M. , Shen , D.‐M. , Chapman , K. T. , Malkowitz , L. , Springer , M. S. , Gould , S. L. , DeMartino , J. A. , Siciliano , S. J. , Cascieri , M. A. , Carella , A. , Carver , G. , Holmes , K. , Schleif , W. A. , Danzeisen , R. , Hazuda , D. , Kessler , J. , Lineberger , J. , Miller , M. and Emini , E. 2003 . CCR5 antagonists: 3‐(Pyrrolidin‐1yl)propionic acid analogues with potent anti‐HIV activity . Organic Lett. , 5 : 2473 – 2475 . [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Limberg , G. , Lundt , I. and Zavilla , J. 1999 . Deoxyiminoalditols from aldonic acids VI. Preparation of the four stereoisomeric 4‐amino‐3‐hydroxypyrrolidines from bromodeoxytetronic acids. Discovery of a new α‐mannosidase inhibitor . Synthesis , : 178 – 183 . [CROSSREF]
   Google Scholar
• Brandi , A. , Cicchi , S. , Paschette , V. , Pardo , D. G. and Cossy , J. 2002 . A new nitrone from C2 symmetric piperidine for the synthesis of hydroxylated indolizinone . Tetrahedron Lett. , 43 : 9357 – 9359 . [CROSSREF]
   Google Scholar
• Walsh , D. A. and Welstead , W. J. Trans‐4‐(2‐chlorophenoxy)‐1‐Ethyl‐3‐Pyrrolidinol and Anti‐depressant Use Thereof . U.S. 4,452,809 . June 5, 1984 .
   Google Scholar
• Walsh , D. A. and Welstead , W. J. Cis and Trans‐3‐Aryloxy‐4‐Hydroxypyrrolidines Used as Anti‐arrhythmics . U.S. 4,585,785 . March 10, 1980 .
   Google Scholar
• Paioni , R. Derivatives of Perhydro‐aza‐Heterocycles . U.S. 4,160,837 . July 10, 1979 .
   Google Scholar
• Enyedy , I. J. , Zaman , W. A. , Sakamuri , S. , Kozikowski , A. P. , Johnson , K. M. and Wang , S. 2001 . Pharmacophore‐based discovery of 3,4‐disubstituted pyrrolidines as a novel class of monoamine transporter inhibitors . BioOrganic Med. Chem. Lett. , 11 : 1113 – 1118 . [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Dubuffet , T. , Muller , O. , Simont , S. S. , Descombes , J.‐J. , Laubie , M. , Verbeuren , T. J. and Lavielle , G. 1996 . Synthesis of new 3,4‐Disubstituted pyrrolidines as thromboxane A2/prostaglandin H2 (TP) receptor antagonists . BioOrganic Med. Chem. Lett. , 6 : 349 – 352 . [CROSSREF]
   Web of Science ®Google Scholar
• Karlsson , S. , Han , F. , Hogberg , H.‐E. and Caldirola , P. 1999 . trans‐3,4‐Disubstituted pyrrolidines by 1,3‐dipolar cycloaddition: enantioselective approaches and their limitations . Tetrahedron: Asymmetry , 10 : 2605 – 2616 . [CROSSREF]
   Google Scholar
• Ma , Z. , Wang , S. , Cooper , C. S. , Kung , A. K.C. , Lynch , J. K. , Plagge , F. and Chu , D. T.W. 1997 . Asymmetric dipolar cycloaddition reactions: a practicle, convergent synthesis of chiral pyrrolidines . Tetrahedron: Asymmetry , 8 : 883 – 887 . [CROSSREF]
   Google Scholar
• Sheldrick , G. M. 1990 . Phase annealing in SHELX‐90: direct methods for larger structures . Acta Crystallogr. , A46 : 467 – 473 .
   Web of Science ®Google Scholar
• Sheldrick , G. M. 1993 . “ Program for Crystal Structure Determination ” . In SHELXL‐93 Germany : University of Göttingen .
   Google Scholar
• Flack , H. D. 1983 . On enantiomorph‐polarity estimation . Acta Crystallogr. , A39 : 876 – 881 .
   Web of Science ®Google Scholar
• Flack , H. D. and Bernardinelli , G. 1999 . Absolute structure and absolute configuration . Acta Crystallogr. , A55 : 908 – 915 .
   Web of Science ®Google Scholar
• Matsunaga , S. , Das , J. , Roels , J. , Vogel , E. M. , Yamamoto , N. , Iida , T. , Yamaguchi , K. and Shibasaki , M. 2000 . Catalytic enantioselective meso‐epoxide ring opening reaaction with phenolic oxygen nucleophilic promoted by gallium heterobimetallic multifunctional complexes . J. Am. Chem. Soc. , 122 : 2252 – 2260 . [CROSSREF]
   Google Scholar
• Iida , T. , Yamamoto , N. , Matsunaga , S. , Woo , H.‐G. and Shibasaki , M. 1998 . Enantioselective ring opening of expoxides with 4‐methoxyphenol catalyzed by gallium heterobimetallic complexes: An efficient method for the synthesis of optically active 1,2‐diol monoethers . Angew. Chem. Int. Ed. , 37 : 2223 – 2226 . [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Schauss , S. E. , Larrow , J. F. and Jacobsen , E. N. 1997 . Practical synthesis of enantiopure cyclic 1,2‐amino alcohols via catalytic asymmetric ring opening of meso‐epoxides . J. Org. Chem. , 62 : 4197 – 4199 . [CROSSREF]
   Google Scholar