Skip to main content
SpringerLink
Log in

Synthesis and Stereostructure of 3-Amino-5- and -6-hydroxybicyclo[2.2.1]heptane-2-carboxylic Acid Diastereomers

  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary.

All-endo-3-amino-5-hydroxybicyclo[2.2.1]heptane-2-carboxylic acid and two epimers of 3-amino-6-hydroxybicyclo[2.2.1]heptane-2-carboxylic acid were prepared via 1,3-oxazine or γ-lactone intermediates by the stereoselective functionalization of endo-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylic acid derivatives. Their structures were proved by IR and NMR spectroscopy, with the use of HMQC, HMBC, DEPT, and DIFFNOE techniques.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Juaristi E (1997) Enantioselective Synthesis of β-Amino Acids. Wiley-VCH, New York

  • F Fringuelli F Pizzo (2003) J Org Chem 68 7041 Occurrence Handle1:CAS:528:DC%2BD3sXmtFOltro%3D

    CAS  Google Scholar 

  • M Ciclosi C Fava R Galeazzi M Orena J Sepulveda-Arques (2002) Tetrahedron Lett 43 2199 Occurrence Handle10.1016/S0040-4039(02)00233-2 Occurrence Handle1:CAS:528:DC%2BD38XhslGksr8%3D

    Article  CAS  Google Scholar 

  • R Roers GL Verdine (2001) Tetrahedron Lett 42 3563 Occurrence Handle1:CAS:528:DC%2BD3MXjtlSksLw%3D

    CAS  Google Scholar 

  • AM Nocioni C Papa C Tomasini (1999) Tetrahedron Lett 40 8453 Occurrence Handle10.1016/S0040-4039(99)01772-4 Occurrence Handle1:CAS:528:DyaK1MXntlKiurc%3D

    Article  CAS  Google Scholar 

  • EGJC Warmerdam RD Van Rijn J Brussee CG Kruse A Van der Gen (1996) Tetrahedron Asymm 7 1723 Occurrence Handle1:CAS:528:DyaK28XjvVKnt7k%3D

    CAS  Google Scholar 

  • O Roy G Pattenden DC Pryde C Wilson (2003) Tetrahedron 59 5115 Occurrence Handle1:CAS:528:DC%2BD3sXkvVKhtL4%3D

    CAS  Google Scholar 

  • HJ Ha GS Park YG Ahn GS Lee (1998) Bioorg Med Chem Lett 8 1619 Occurrence Handle10.1016/S0960-894X(98)00271-6 Occurrence Handle1:CAS:528:DyaK1cXkvValur8%3D

    Article  CAS  Google Scholar 

  • RA Tromp M Van der Hoeven A Amore J Brussee M Overhand GA Van der Marel A Van der Gen (2001) Tetrahedron Asymm 12 1109 Occurrence Handle10.1016/S0957-4166(01)00193-8 Occurrence Handle1:CAS:528:DC%2BD3MXksFOisLs%3D

    Article  CAS  Google Scholar 

  • MA Cuifolini T Shimizu S Swaminathan N Xi (1997) Tetrahedron Lett 38 4947

    Google Scholar 

  • F Fülöp (2001) Chem Rev 101 2181

    Google Scholar 

  • A Avenoza C Cativiela M Paris JM Peregrina B Saenz-Torre (1997) Tetrahedron Asymm 8 1123 Occurrence Handle1:CAS:528:DyaK2sXivVeitbg%3D

    CAS  Google Scholar 

  • C Cinquin M Bortolussi R Bloch (1996) Tetrahedron Asymm 7 3327 Occurrence Handle10.1016/0957-4166(96)00434-X Occurrence Handle1:CAS:528:DyaK28XntlGisro%3D

    Article  CAS  Google Scholar 

  • H Suga N Tanimoto AJ Sinskey S Masamune (1994) J Am Chem Soc 116 11197 Occurrence Handle1:CAS:528:DyaK2MXhvFyqt7c%3D

    CAS  Google Scholar 

  • S Kobayashi K Kamiyama M Ohno (1990) J Org Chem 55 1169 Occurrence Handle1:CAS:528:DyaK3cXpvFSlug%3D%3D

    CAS  Google Scholar 

  • Avenoza A, Cativiela C, Fernandez-Recio MA, Peregrina MJ (1995) Synlett 891

  • P Sohár G Stájer G Bernáth (1983) Org Magn Resonance 21 512

    Google Scholar 

  • P Sohár I Pelczer G Stájer G Bernáth (1987) Magn Reson Chem 25 584

    Google Scholar 

  • F Miklós P Sohár A Csámpai R Sillanpää M Péter G Stájer (2002) Heterocycles 57 2309

    Google Scholar 

  • Sohár P (1983) Nuclear Magnetic Resonance Spectroscopy, vol 2. CRC Press, Boca Raton, Florida

  • Holly S, Sohár P (1975) In: Láng L, Prichard WH (eds) Theoretical and Technical Introduction to the Series “Absorption Spectra in the Infrared Region”. Akadémiai Kiadó, Budapest, p 95

  • The compounds discussed in this paper are racemates. The Schemes show only the enantiomers of the starting compounds 1 and 5 in which C–1 and C–3 have (S), while C–2 and C–4 have (R) configurations. IUPAC Nomenclature of Organic Chemistry, Section F, Stereochemistry, Pure Appl Chem (1976) 45: 11

  • G Stájer EA Szabó F Fülöp G Bernáth (1983) J Heterocyclic Chem 20 1181 Occurrence Handle10.1002/jhet.5570200509

    Article  Google Scholar 

  • P Canonne M Akssira A Dahdouh H Kasmi M Boumzebra (1993) Tetrahedron 49 1985 Occurrence Handle10.1016/S0040-4020(01)86298-0 Occurrence Handle1:CAS:528:DyaK3sXkt1yjtbg%3D

    Article  CAS  Google Scholar 

  • G Stájer EA Szabó F Fülöp G Bernáth P Sohár (1984) J Heterocyclic Chem 21 1373

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Pharmaceutical Chemistry, University of Szeged, H-6701, POB 121, Hungary

    Márta Palkó, Elvira Sándor & Ferenc Fülöp

  2. Research Group for Structural Chemistry and Spectroscopy, Hungarian Academy of Sciences and Institute of General and Inorganic Chemistry, Eötvös Lóránd University, H-1518, POB 32, Budapest, Hungary

    Pál Sohár

Authors
  1. Márta Palkó
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Elvira Sándor
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pál Sohár
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ferenc Fülöp
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ferenc Fülöp.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Palkó, M., Sándor, E., Sohár, P. et al. Synthesis and Stereostructure of 3-Amino-5- and -6-hydroxybicyclo[2.2.1]heptane-2-carboxylic Acid Diastereomers. Monatsh. Chem. 136, 2051–2058 (2005). https://doi.org/10.1007/s00706-005-0369-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-005-0369-9

Search

Navigation