Enantioselective intramolecular CH-insertions upon Cu-catalyzed decomposition of phenyliodonium ylides

Molecules

Volumn 6, Issue 3, 2001, Pages 258-266

  Müller, Paul ^a   Boléa, Christelle ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Asymmetric induction; CH insertion; Cu catalysis; Phenyliodonium ylides

Indexed keywords

COPPER; IODINE DERIVATIVE; PHENYLIODONIUM; UNCLASSIFIED DRUG;

CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHIRALITY; CONFERENCE PAPER; DECOMPOSITION; ENANTIOSELECTIVITY; REACTION ANALYSIS;

EID: 0042498040     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/60300258     Document Type: Conference Paper

References (33)

1. Camacho, M. B.; Clark, A. E.; Liebrecht, T. A.; DeLuca, J. P. A phenyliodonium ylide as a precursor for dicarboethoxycarbenes: Demonstration of a strategy for carbene generation. J. Am. Chem. Soc. 2000, 122, 5210-5211.
2. Hayasi, Y.; Okada, T.; Kawanisi, M. Cyclic diacylcarbenes generated from iodonium ylides and diazodiketones. Bull. Chem. Soc. Jpn. 1970, 43, 2506-2511.
3. Hadjiarapoglou, L.; Varvoglis, A.; Alcock, N. W.; Pike, G. A. Reactivity of Phenyliodonium bis(arylsulphonyl)methylides towards alkenes and alkynes: Crystal structure of 9-phenylsulfonyl-1,2,3,4,4a,9a-hexahydro-1,4- methanofluorene. J. Chem. Soc. Perkin Trans. 1 1988, 2839-2846; Hadjiarapoglou, L.; Spyroudis, S.; Varvoglis, A. Phenyliodonium bis(phenylsulfonyl)methylide: A new hypervalent iodonium ylide. J. Am. Chem. Soc. 1985, 107, 7178-7179; Hadjiarapoglou, L. The chemistry of photolytically and thermally generated α-ketocarbenes from iodonium ylides of β-diketones. Tetrahedron Lett. 1987, 28, 4449-4450.
4. Hadjiarapoglou, L.; Varvoglis, A.; Alcock, N. W.; Pike, G. A. Reactivity of Phenyliodonium bis(arylsulphonyl)methylides towards alkenes and alkynes: Crystal structure of 9-phenylsulfonyl-1,2,3,4,4a,9a-hexahydro-1,4- methanofluorene. J. Chem. Soc. Perkin Trans. 1 1988, 2839-2846; Hadjiarapoglou, L.; Spyroudis, S.; Varvoglis, A. Phenyliodonium bis(phenylsulfonyl)methylide: A new hypervalent iodonium ylide. J. Am. Chem. Soc. 1985, 107, 7178-7179; Hadjiarapoglou, L. The chemistry of photolytically and thermally generated α-ketocarbenes from iodonium ylides of β-diketones. Tetrahedron Lett. 1987, 28, 4449-4450.
5. Hadjiarapoglou, L.; Varvoglis, A.; Alcock, N. W.; Pike, G. A. Reactivity of Phenyliodonium bis(arylsulphonyl)methylides towards alkenes and alkynes: Crystal structure of 9-phenylsulfonyl-1,2,3,4,4a,9a-hexahydro-1,4- methanofluorene. J. Chem. Soc. Perkin Trans. 1 1988, 2839-2846; Hadjiarapoglou, L.; Spyroudis, S.; Varvoglis, A. Phenyliodonium bis(phenylsulfonyl)methylide: A new hypervalent iodonium ylide. J. Am. Chem. Soc. 1985, 107, 7178-7179; Hadjiarapoglou, L. The chemistry of photolytically and thermally generated α-ketocarbenes from iodonium ylides of β-diketones. Tetrahedron Lett. 1987, 28, 4449-4450.
6. (a) Hood, J. N. C.; Lloyd, D.; McDonald, W. A.; Shepherd, T. M. The effects of different copper (and some other) catalysts on the conversion of triphenyl- and tetraphenyl-diazocyclopentadienes and of some phenyliodonium α,α′-dicarbonylylides into arsonium and other ylides. Tetrahedron 1982, 38, 3355-3358.
7. (b) Saito, T.; Kikuchi, K.; Kondo, A. A new and simple synthesis of heterocycle-fused [c]thiophenes: Reaction of heteroaromatic thioketones with bis(arylsulfonyl)diazomethanes and phenyliodonium bis(phenylsulfonyl)-methylide. Synthesis 1995, 87-91; Saito, T.; Gon, S.; Kikuchi, H.; Motoki, S. J. Chem. Res. (S) 1994, 2; J. Chem. Res. (M) 1994, 223-235. Fairfax, D. J.; Austin, D. J.; Xu, S. L.; Padwa, A. Alternatives to α-diazo ketones for tandem cyclization-cycloaddition and carbenoid-alkyne metathesis strategies. Novel cyclic enol ether formation via carbonyl ylide rearrangement reactions. J. Chem. Soc. Perkin Trans. 1 1992, 2837-2844.
8. (b) Saito, T.; Kikuchi, K.; Kondo, A. A new and simple synthesis of heterocycle-fused [c]thiophenes: Reaction of heteroaromatic thioketones with bis(arylsulfonyl)diazomethanes and phenyliodonium bis(phenylsulfonyl)-methylide. Synthesis 1995, 87-91; Saito, T.; Gon, S.; Kikuchi, H.; Motoki, S. J. Chem. Res. (S) 1994, 2; J. Chem. Res. (M) 1994, 223-235. Fairfax, D. J.; Austin, D. J.; Xu, S. L.; Padwa, A. Alternatives to α-diazo ketones for tandem cyclization-cycloaddition and carbenoid-alkyne metathesis strategies. Novel cyclic enol ether formation via carbonyl ylide rearrangement reactions. J. Chem. Soc. Perkin Trans. 1 1992, 2837-2844.
9. (b) Saito, T.; Kikuchi, K.; Kondo, A. A new and simple synthesis of heterocycle-fused [c]thiophenes: Reaction of heteroaromatic thioketones with bis(arylsulfonyl)diazomethanes and phenyliodonium bis(phenylsulfonyl)-methylide. Synthesis 1995, 87-91; Saito, T.; Gon, S.; Kikuchi, H.; Motoki, S. J. Chem. Res. (S) 1994, 2; J. Chem. Res. (M) 1994, 223-235. Fairfax, D. J.; Austin, D. J.; Xu, S. L.; Padwa, A. Alternatives to α-diazo ketones for tandem cyclization-cycloaddition and carbenoid-alkyne metathesis strategies. Novel cyclic enol ether formation via carbonyl ylide rearrangement reactions. J. Chem. Soc. Perkin Trans. 1 1992, 2837-2844.
10. (b) Saito, T.; Kikuchi, K.; Kondo, A. A new and simple synthesis of heterocycle-fused [c]thiophenes: Reaction of heteroaromatic thioketones with bis(arylsulfonyl)diazomethanes and phenyliodonium bis(phenylsulfonyl)-methylide. Synthesis 1995, 87-91; Saito, T.; Gon, S.; Kikuchi, H.; Motoki, S. J. Chem. Res. (S) 1994, 2; J. Chem. Res. (M) 1994, 223-235. Fairfax, D. J.; Austin, D. J.; Xu, S. L.; Padwa, A. Alternatives to α-diazo ketones for tandem cyclization-cycloaddition and carbenoid-alkyne metathesis strategies. Novel cyclic enol ether formation via carbonyl ylide rearrangement reactions. J. Chem. Soc. Perkin Trans. 1 1992, 2837-2844.
11. (a) Müller, P.; Fernandez, D. Carbenoid reactions in rhodium(II)-catalyzed decomposition of iodonium ylides. Helv. Chim. Acta 1995, 78, 947-958;
12. (b) Müller, P.; Fernandez, D.; Nury, P.; Rossier, J.-C. Metal-catalyzed carbenoid reactions with iodonium and sulfonium ylides. J. Phys. Org. Chem. 1998, 11, 321-333.
13. (a) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides; Wiley, New York, 1998, Chapter 2.
14. (b) Doyle, M. P.; Forbes, D. C. Recent advances in asymmetric catalytic metal carbene transformations. Chem. Rev. 1998, 98, 911-935.
15. (a) Moriarty, R. M.; Prakash, O.; Vaid, R. K.; Zhao L. A novel intramolecular cyclopropanation using iodonium ylides. J. Am. Chem. Soc. 1989, 111, 6443-6444.
16. Moriarty, R. M.; Kim, J.; Guo, L. Intramolecular cyclopropanation using iodonium ylides: The 3,5-cyclovitamin D ring A synthon. Tetrahedron Lett. 1993, 34, 4129-4132;
17. Moriarty, R. M.; May, E. J.; Prakash, O. Intramolecular cyclization of aryl substituted iodonium ylides with copper(I) chloride. Tetrahedron Lett. 1997, 38, 4333-4336.
18. (b) Gallos, J. K.; Koftis, T. V.; Koumbis, A. E. Synthesis of enantiomerically pure bicyclo[3.1.0]hexanes from D-ribose by intramolecular cyclopropanation. J. Chem. Soc. Perkin Trans. 1 1994, 611-612.
19. Müller, P.; Boléa, C. Asymmetric induction in Cu-catalyzed intramolecular cyclopropanations of phenyliodonium ylides. Synlett 2000, 826-828.
20. th electronic Conference on Synthetic Organic Chemistry, ecsoc.-4:http://www.mdpi.org/ecsoc-4a0015/0015.htm
21. Hashimoto, S.; Watanabe, N.; Sato, T.; Shiro, M.; Ikegami, S. Enhancement of enantioselectivity in intramolecular CH-insertion reactions of α-diazo β-keto esters catalyzed by chiral dirhodium(II) carboxylates. Tetrahedron Lett. 1993, 32, 5109-5112;
22. Hashimoto, S.; Watanabe, N.; Ikegami, S. Enantioselective intramolecular CH insertion reactions of α-diazo β-keto esters catalyzed by dirhodium(II) tetrakis[N-phthaloyl-(S)-phenylalaninate]: The effect of the substituent at the insertion site on enantioselectivity. Synlett 1994, 353-355;
23. Hashimoto, S.; Watanabe, N.; Kawano, K.; Ikegami, S. Double asymmetric induction in intramolecular CH insertion reactions of α-diazo β-keto esters. Synth. Commun. 1994, 24, 3277-3287.
24. Schank, K.; Lick, C. Ozonolytic fragmentation of phenyliodonium β-diketonates, a convenient synthesis of unsolvated vic-triketones. Synthesis 1983, 392-395.
25. Müller, P.; Maîtrejean, E. Rhodium(II)- and copper(I)-catalyzed intramolecular carbon-hydrogen bond insertions with metal carbenoids derived from diazo ketones. Collect. Czech. Chem. Commun. 1999, 64, 1807-1825.
26. Doyle, M. P.; Davies, S. B.; Hu, W. Dirhodium(II) tetrakis[methyl 2-oxaazetidine-4-carboxylate]: A chiral dirhodium(II) carboxamidate of exceptional reactivity and selectivity. Org. Lett. 2000, 2, 1145-1147.
27. Doyle, M. P.; Winchester, W. R.; Protopopova, M. N.; Müller, P.; Bernardinelli, G.; Ene, D.; Motallebi, S. Tetrakis[(4S)-4-phenyloxazolidin-2- one]dirhodium(II) and its catalytic applications for metal carbene transformations. Helv. Chim. Acta 1993, 76, 2227-2235;
28. Müller, P.; Nury, P. Desymmetrization of meso-N-sulfonated aziridines with chiral nonracemic nucleophiles and bases. Helv. Chim. Acta 2000, submitted.
29. Andrus, M. B.; Asgari, D.; Sclafani, J. A. Efficient synthesis of 1,1′-binaphthyl and 2,2′-bi-o-tolyl-2,2′-bis(oxazoline)s and preliminary use for the catalytic asymmetric allylic oxidation of cyclohexene. J. Org. Chem. 1997, 62, 9365-9368.
30. Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Conformationally constrained bis(oxazoline) derived chiral catalysts: A highly effective enantioselective Diels-Alder Reaction. Tetrahedron Lett. 1996, 37, 3815-1818.
31. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. Bis(oxazolines) as chiral ligands in metal-catalyzed asymmetric reactions. Catalytic asymmetric cyclopropanation of olefins. J. Am. Chem. Soc. 1991, 113, 726-728;
32. Evans, D. A.; Peterson, G. S.; Johnson, J. S.; Barnes, D. M.; Campos, K. R.; Woerpel, K. A. An improved procedure for the preparation of 2,2-bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane [(S,S)-tert-butyl bis(oxazoline)] and derived copper(II) complexes. J. Org. Chem. 1998, 63, 4541-4544.
33. Müller, P.; Boléa, C. Carbenoid pathways in Cu-catalyzed intramolecular cyclopropanations of phenyliodonium ylides. Helv. Chim. Acta 2001, in preparation.