Synthesis of the rac-6-hydroxy-3-methoxycyclohex-2-enone and resolution through recrystallization of its diastereomeric N-tosyl-(S)-proline esters

Chirality

Volumn 12, Issue 4, 2000, Pages 287-290

  Zaitsev, V G ^a   Sachava, D G ^a   Yankovskaya, G S ^a   Garbuz, N I ^a  

^a INSTITUTE OF BIOORGANIC CHEMISTRY   (Belarus)

Author keywords

1H NMR based conformational assignment; Absolute configuration; Circular dichroism; Cotton effect; Diastereomeric enrichment; N tosyl (S) proline; Racemic alcohol

Indexed keywords

6 HYDROXY 3 METHOXYCYCLOHEX 2 ENONE; ESTER DERIVATIVE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

CHIRALITY; CONFERENCE PAPER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RUSSIAN FEDERATION; SYNTHESIS;

EID: 0034099967     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(2000)12:4<287::AID-CHIR15>3.0.CO;2-N     Document Type: Conference Paper

References (8)

1. Méthodes de dédoublement. In: Velluz L, editor. Substances naturelles de Synthése, vol. IX. Paris: Massen et Cie; 1954. p 119-174.
2. Snazke G. Modifizierung de Oktanregel für α,β-ungesättigte Ketone: Theorie. Tetrahedron 1965;21:413-419, and references therein.
3. Gebauer O, Brückner R. A practical synthesis of enantiopure (R)-4-hydroxy-2-cyclohexen-1-one. Liebigs Ann 1996:1559-1563, and references therein.
4. Zaitsev VG, Polozov GI, Lakhvich FA. Synthesis of 2-acyl-4-hydroxycyclohexane-1,3-diones, kairomones and defensive compounds of some insects. Tetrahedron 1994;50:6377-6386.
5. High activity Raney Nickel, W2, according to W-grades published in Billica HR, Adkins H. Org Syntheses, Coll. Vol. III, 176, 1955, was prepared from Ni/Al alloy and KOH (or NaOH): Organikum. 18., berichtigte Auflage. Berlin: Deutscher Verlag der Wissenschaften, 1990:655.
6. High activity Raney Nickel, W2, according to W-grades published in Billica HR, Adkins H. Org Syntheses, Coll. Vol. III, 176, 1955, was prepared from Ni/Al alloy and KOH (or NaOH): Organikum. 18., berichtigte Auflage. Berlin: Deutscher Verlag der Wissenschaften, 1990:655.
7. Pravda Z, Rudinger J. Amino-acids and peptides. XII. A synthesis of L-proline from L-glutamic acid. Coll Czech Chem Comm 1955;20: 1-8.
8. Beecham AF. Tosyl-α-amino acids. Degradation of the acid chlorides and azides by aqueous alkali. J Am Chem Soc 1957;79:3257-3261.