Unique reactivity of α,β-unsaturated carboxylic acid imidazolides: Catalytic asymmetric synthesis of α,β-epoxy esters and α,β-epoxy carboxylic acid derivatives

Chirality

Volumn 15, Issue 4, 2003, Pages 306-311

  Nemoto, Tetsuhiro ^a   Tosaki, Shin Ya ^a   Ohshima, Takashi ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

, epoxy esters; , epoxy peroxy tert butyl esters; Catalytic asymmetric epoxidation; La BINOL Ph3As=O complex; , unsaturated carboxylic acid imidazolides

Indexed keywords

ALDEHYDE; ALPHA,BETA CARBOXYLIC ACID DERIVATIVE; ALPHA,BETA EPOXYALDEHYDE DERIVATIVE; ALPHA,BETA EPOXYAMIDE DERIVATIVE; ALPHA,BETA UNSATURATED CARBOXYLIC ACID IMIDAZOLIDE DERIVATIVE; AMIDE; CARBOXYLIC ACID DERIVATIVE; EPOXIDE; ESTER; GAMMA,DELTA EPOXY BETA KETO ESTER; IMIDAZOLE DERIVATIVE; METHANOL; METHYL GROUP; UNCLASSIFIED DRUG;

CATALYSIS; CATALYST; CHEMICAL REACTION; CONFERENCE PAPER; ENANTIOMER; ENERGY; EPOXIDATION; PRIORITY JOURNAL; PRODUCTIVITY; SYNTHESIS;

EID: 0037263567     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10205     Document Type: Conference Paper

References (20)

1. For recent reviews: (a) Porter MJ, Skidmore J. Asymmetric epoxidation of electron-deficient olefins. Chem Commun 2000;1215-1225.
2. (b) Nemoto T, Ohshima T, Shibasaki M. Catalytic asymmetric epoxidation of α,β-unsaturated carbonyl compounds. J Synth Org Chem Jpn 2002; 60:94-105.
3. (a) Nemoto T, Ohshima T, Shibasaki M. Enantioselective total syntheses of nobel PKC activator (+)-decursin and its derivatives using catalytic asymmetric epoxidation of an enone. Tetrahedron Lett 2000;41:9569-9574.
4. (b) Corey EJ, Zhang F-Y. Mechanism and conditions for highly enantioselective epoxidation of α,β-enones using charge-accelerated catalysis by a rigid quaternary ammonium salt. Org Lett 1999;1:1287-1290.
5. (c) Carde L, Davis H, Geller TP, Roberts SM. Paa-Sicats: powerful catalysts for asymmetric epoxidation of enones. novel syntheses of α-arylpropanoic acids including (S)-fenoprofen. Tetrahedron Lett 1999;40:5421-5424.
6. (a) Bougauchi M, Watanabe S, Arai T, Sasai H, Shibasaki M. Catalytic asymmetric epoxidation of α,β-unsaturated ketones promoted by lanthanoid complexes. J Am Chem Soc 1997;119:2329-2330.
7. (b) Watanabe S, Kobayashi Y, Arai T, Sasai H, Shibasaki M. Water vs. desiccant. improvement of Yb-BINOL complex catalyzed enantioselective epoxidation of enones. Tetrahedron Lett 1998;39:7353-7356.
8. (c) Watanabe S, Arai T, Sasai H, Bougauchi M, Shibasaki M. The first catalytic enantioselective synthesis of cis-epoxyketones from cis-enone. J Org Chem 1998;63:8090-8091.
9. 3As=O complex: structural determination of the asymmetric catalyst. J Am Chem Soc 2001;123:2725-2732.
10. Jacobsen EN, Deng L, Furukawa Y, Martinez LE. Enantioselective catalytic epoxidation of cinnamate esters. Tetrahedron 1994;50:4323-4334.
11. (a) Armstrong A, Hayter BR. Catalytic enantioselective epoxidation of alkenes with a tropinone-derived chiral ketone. Chem Commun 1998;621-622.
12. (b) Solladié-Cavallo A, Bouérat L. Epoxidation of p-methoxycinnamates using chiral dioxiranes derived from new trisubstituted halogenated cyclohexanones: enhanced efficiency of ketones having an axial halogen. Org Lett 2000;2:3531-3534.
13. 2 symmetric chiral ketone for catalytic asymmetric epoxidation of unfunctionalized olefins. J Am Chem Soc 1996;118:491-492.
14. 2 symmetric chiral ketone for catalytic asymmetric epoxidation of unfunctionalized olefins. J Am Chem Soc 1996;118:491-492.
15. (d) Wu X-Y, She X, Shi Y. Highly enantioselective epoxidation of α,β-unsaturated esters by chiral dioxirane. J Am Chem Soc 2002;124:8792-8793.
16. Nemoto T, Ohshima T, Shibasaki M. Catalytic asymmetric synthesis of α,β-epoxy esters, aldehydes, amides, and γ,δ-epoxy β-keto esters: unique reactivity of α,β-unsaturated carboxylic acid imidazolides. J Am Chem Soc 2001;123:9474-9475.
17. For a review: Ager DJ, Prakash I, Schaad DR. Chiral oxazolidinones in asymmetric synthesis. Aldrichchim Acta 1997;30:3-12.
18. For an example: Page PCB, Gareh MT, Porter A. N-Acyl imidazoles: excellent acyl electrophiles for 1,3-dithiane oxide anions. Tetrahedron Lett 1993;34:5159-5162 and references therein.
19. For a recent example: Imashiro R, Kuroda T. Asymmetric synthesis of methyl (2R,3S)-3-(4-methoxyphenyl) glycidate, a key intermeditate of diltiazem, via Mukaiyama aldol reaction. Tetrahedron Lett 2001;42:1313-1315 and references therein.
20. Daikai K, Kamaura M, Inanaga J. Remarkable ligand effect on the enantioselectivity of the chiral lanthanum complex-catalyzed asymmetric epoxidation of enones. Tetrahedron Lett 1998;39:7321-7322.