Synthesis and enantioselective rearrangement of (Z)-4-triphenylmethoxy-2,3- epoxybutan-1-ol enantiomers

Chirality

Volumn 19, Issue 3, 2007, Pages 197-202

  Faigl, Ferenc ^a,b   Thurner, Angelika ^b   Farkas, Ferenc ^a   Battancs, Melinda ^a   Poppe, László ^a  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

Author keywords

Chiral oxetane; Enantioselective rearrangement; Enzymatic resolution; Optically active oxirane; Organometallic reagents; Superbases

Indexed keywords

1 HYDROXY 4 TRIPHENYLMETHOXY 2,3 EPOXYBUTANOL DERIVATIVE; 3 [1 HYDROXY 2 (TRIPHENYLMETHOXY)ETHYL] 2 PHENYLOXETANE; 4 TRIPHENYLMETHOXY 2,3 EPOXYBUTAN 1 OL; AMANO LIPASE; BUTANOL; ENZYME; EPOXIDE; ETHYLENE OXIDE DERIVATIVE; LIPOZYME; OXETANE DERIVATIVE; TRITYL DERIVATIVE; UNCLASSIFIED DRUG; VINYL ACETATE;

ARTICLE; BENZYLATION; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CORRELATION ANALYSIS; CRYSTALLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; HYDROLYSIS; PRIORITY JOURNAL; SYNTHESIS;

BUTANOLS; EPOXY COMPOUNDS; STEREOISOMERISM; TRITYL COMPOUNDS;

EID: 33847204710     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20361     Document Type: Article

References (13)

1. Ichikawa E, Kato K. Syntheses of oxetanocin A and related unusual nucleosides with bis(hydroxymethyl)-branched sugars. Synthesis 2002; 1-28.
2. Kidwai MK, Goel Y, Srivastava KC. Oxiranes with quinoline substitution: stereoselective synthesis and antiviral activity. Bioorg Med Chem Lett 1996;6:871-874.
3. Wang M, Cornett B, Nettles J, Liotta DC, Snyder JP. The oxetane ring in taxol. J Org Chem 2000;65:1059-1068.
4. Mordini A, Bindi S, Pecchi S, Degl'Innocenti A, Reginato G, Serci A. Different pathways in the base-promoted isomerization of benzyl oxiranyl ethers. J Org Chem 1996;61:4374-4378.
5. Thurner A, Faigl F, Toke L, Mordini A, Vallachi M, Reginato G, Czira G. Useful base promoted elaborations of oxiranyl ethers. Tetrahedron 2001;57:8173-8180.
6. Thurner A, Faigl F, Mordini A, Bigi A, Reginato G, Toke L. A new base promoted rearrangement of (E)-1-benzyloxy-2,3-epoxyalkanes. Tetrahedron 1998;54:11597-11602.
7. Gao Y, Hanson RM, Klunder JM, Ko SY, Masamune H, Sharpless KB. Catalytic asymmetric epoxidation and kinetic resolution: modified procedures including in situ derivatization. J Am Chem Soc 1987;109:5765-5780.
8. Faigl F, Thurner A, Tárkányi G, Kovári J, Mordini A. Resolution and enantioselective rearrangements of amino group containing oxiranyl ethers. Tetrahedron: Asymmetry 2002;13:59-68.
9. Faigl F, Thurner A, Battancs M, Farkas F, Poppe L, Bódai V, Kmecz I, Simándi I. Efficient, scalable kinetic resolution of cis-4-benzyloxymethyl-2,3-epoxybutanol. Tetrahedron: Asymmetry 2005;16:3841-3847.
10. Makino K, Ichikawa Y. Synthesis of a 2-deoxy-ribose type 1-N-iminosugar. Tetrahedron Lett 1998;39:8245-8248.
11. Azzena F, Calvani F, Crotti P, Gardelli C, Macchia F, Pineschi M. Regiochemical control of the ring opening of 1:2-epoxides by means of chelating processes. 10. Synthesis and ring opening reactions of mono- and difunctionalized cis and trans aliphatic oxirane systems. Tetrahedron 1995;51:10601-10626.
12. Chen CS, Fujimoto Y, Girdaukas G, Sih CJ. Quantitative analyses of biochemical kinetic resolutions of enantiomers. J Am Chem Soc 1982;104:7294-7299.
13. Bessodes M, Komiotis D, Antonakis K. Rapid and selective detritylation of primary alcohols using formic acid. Tetrahedron Lett 1986;27:579-580.