Polymer-supported 2,2′-bis(oxazolin-2-yl)- 1,1′-binaphthyls (boxax): Immobilized chiral ligands for asymmetric wacker-type cyclizations

Synlett

Volumn , Issue 12, 2002, Pages 2049-2053

  Hocke, Heiko ^a   Uozumi, Yasuhiro ^a  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

Asymmetric catalysis; Boxax; Immobilized chiral catalysts; Wacker type cyclization

Indexed keywords

DIHYDROBENZOFURAN DERIVATIVE; LIGAND; MACROGOL; NAPHTHYL GROUP; OXAZOLINE DERIVATIVE; PALLADIUM COMPLEX; PHENOL DERIVATIVE; POLYMER;

ARTICLE; BROMINATION; CATALYSIS; CHIRALITY; CYCLIZATION; ENANTIOSELECTIVITY; ESTERIFICATION; HYDROGENATION; REACTION ANALYSIS;

EID: 0036456056     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35603     Document Type: Article

References (51)

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2. For reviews, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Burgess, K.; Porte, A. M. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: Greenwich, 1997, 2, 69. (d) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (e) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000.
3. For reviews, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Burgess, K.; Porte, A. M. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: Greenwich, 1997, 2, 69. (d) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (e) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000.
4. For reviews, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Burgess, K.; Porte, A. M. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: Greenwich, 1997, 2, 69. (d) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (e) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000.
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6. For studies on polymer-supported palladium catalysts reported by the author's group, see: (a) π-Allylic substitution: Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557. (b) Asymmetric allylic substitution: Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (c) π-Allylic substitution: Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (d) Cross-coupling: Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384. (e) Carbonylation reaction: Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921. (f) Asymmetric allylic substitution: Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (g) Cross-coupling: Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997. (h) Sonogashira reaction: Uozumi, Y.; Kobayashi, Y. Heterocycles 2002, in press
7. For studies on polymer-supported palladium catalysts reported by the author's group, see: (a) π-Allylic substitution: Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557. (b) Asymmetric allylic substitution: Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (c) π-Allylic substitution: Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (d) Cross-coupling: Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384. (e) Carbonylation reaction: Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921. (f) Asymmetric allylic substitution: Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (g) Cross-coupling: Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997. (h) Sonogashira reaction: Uozumi, Y.; Kobayashi, Y. Heterocycles 2002, in press
8. For studies on polymer-supported palladium catalysts reported by the author's group, see: (a) π-Allylic substitution: Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557. (b) Asymmetric allylic substitution: Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (c) π-Allylic substitution: Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (d) Cross-coupling: Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384. (e) Carbonylation reaction: Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921. (f) Asymmetric allylic substitution: Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (g) Cross-coupling: Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997. (h) Sonogashira reaction: Uozumi, Y.; Kobayashi, Y. Heterocycles 2002, in press
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13. For studies on polymer-supported palladium catalysts reported by the author's group, see: (a) π-Allylic substitution: Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557. (b) Asymmetric allylic substitution: Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (c) π-Allylic substitution: Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (d) Cross-coupling: Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384. (e) Carbonylation reaction: Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921. (f) Asymmetric allylic substitution: Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (g) Cross-coupling: Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997. (h) Sonogashira reaction: Uozumi, Y.; Kobayashi, Y. Heterocycles 2002, in press
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35. 25-7.28 (c 0.49, THF).
36. ArgoGel amino resin (1% DVB cross-linked) purchased from Argonaut Technologies Inc. was used.
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43. 13C-MASNMR data of 4a-d: 4a: δ = 17.92, 18.25, 31.35, 32.36, 37.33, 39.01, 69.64, 72.08, 124.86, 125.39, 131.29, 132.62, 133.79, 134.04, 134.12, 137.33, 137.63, 139.31, 163.31, 171.63.4b: δ = 31.26, 37.12, 38.94, 74.10, 131.23, 132.58, 133.97, 134.27, 137.46, 137.81, 139.70, 142.05, 164.68, 171.68.4c: δ = 25.21, 31.34, 33.27, 37.43, 39.00, 67.74, 75.75, 124.66, 125.18, 131.39, 132.69, 133.95, 134.18, 137.74, 137.81, 138.02, 139.28, 162.75, 171.68. 4d: δ = 27.67, 31.30, 37.29, 39.00, 66.53, 78.96, 125.40, 131.17, 132.50, 133.60, 133.88, 136.54, 136.82, 139.35, 163.06, 171.59.
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45. General Procedure for the Asymmetric Wacker-Type Cyclization of 1: A mixture of immobilized catalyst (0.02 mmol Pd), 2-(2,3-dimethyl-2-butenyl)-phenol(1) (0.2 mmol, 35.2 mg), benzoquinone (0.8 mmol, 86.4 mg) and MeOH (1 mL) was agitated at 60°C with shaking for 20 h. After being cooled to r.t., the resin was filtered off and washed twice with MeOH (1 mL). The solvent was removed in vacuo and the residue was purified by column chromatography using silica gel and n-hexane-EtOAc (95:5) giving (S)-2-isopropenyl-2-methyl-2,3-dihydrobenzofuran(2) as colorless oil. The ee was determined by GC (chiral stationary phase capillary column Cyclodex CB).
46. For recent examples of PEG-supported binaphthyl-based chiral catalysts, see: (a) Guerreiro, P.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Dellis, P. Tetrahedron Lett. 2001, 42, 3423. (b) Fan, Q.-H.; Deng, G.-J.; Lin, C.-C.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1241. (c) Yang, X.-W.; Sheng, J.-H.; Da C, S.; Wang, H.-S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295. (d) Fan, Q.-H.; Deng, G.-J.; Chen, X.-M.; Xie, W.-C.; Jiang, D.-Z.; Liu, D.-S.; Chan, A. S. C. J. Mol. Cat. A. 2000, 159, 37; see also ref. 2b.
47. For recent examples of PEG-supported binaphthyl-based chiral catalysts, see: (a) Guerreiro, P.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Dellis, P. Tetrahedron Lett. 2001, 42, 3423. (b) Fan, Q.-H.; Deng, G.-J.; Lin, C.-C.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1241. (c) Yang, X.-W.; Sheng, J.-H.; Da C, S.; Wang, H.-S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295. (d) Fan, Q.-H.; Deng, G.-J.; Chen, X.-M.; Xie, W.-C.; Jiang, D.-Z.; Liu, D.-S.; Chan, A. S. C. J. Mol. Cat. A. 2000, 159, 37; see also ref. 2b.
48. For recent examples of PEG-supported binaphthyl-based chiral catalysts, see: (a) Guerreiro, P.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Dellis, P. Tetrahedron Lett. 2001, 42, 3423. (b) Fan, Q.-H.; Deng, G.-J.; Lin, C.-C.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1241. (c) Yang, X.-W.; Sheng, J.-H.; Da C, S.; Wang, H.-S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295. (d) Fan, Q.-H.; Deng, G.-J.; Chen, X.-M.; Xie, W.-C.; Jiang, D.-Z.; Liu, D.-S.; Chan, A. S. C. J. Mol. Cat. A. 2000, 159, 37; see also ref. 2b.
49. For recent examples of PEG-supported binaphthyl-based chiral catalysts, see: (a) Guerreiro, P.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Dellis, P. Tetrahedron Lett. 2001, 42, 3423. (b) Fan, Q.-H.; Deng, G.-J.; Lin, C.-C.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1241. (c) Yang, X.-W.; Sheng, J.-H.; Da C, S.; Wang, H.-S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295. (d) Fan, Q.-H.; Deng, G.-J.; Chen, X.-M.; Xie, W.-C.; Jiang, D.-Z.; Liu, D.-S.; Chan, A. S. C. J. Mol. Cat. A. 2000, 159, 37; see also ref. 2b.
50. For recent examples of PEG-supported chiral oxazoline ligands, see: (a) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Pitillo, M. J. Org. Chem. 2001, 66, 3160. (b) Glos, M.; Reiser, O. Org. Lett. 2000, 2, 2045.
51. For recent examples of PEG-supported chiral oxazoline ligands, see: (a) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Pitillo, M. J. Org. Chem. 2001, 66, 3160. (b) Glos, M.; Reiser, O. Org. Lett. 2000, 2, 2045.