Enantioselective radical-mediated reduction of α-alkyl-α- iododihydrocoumarins in the presence of a chiral magnesium iodide

Tetrahedron

Volumn 55, Issue 34, 1999, Pages 10295-10304

  Murakata, Masatoshi ^a   Tsutsui, Hideyuki ^a   Takeuchi, Naoto ^a   Hoshino, Osamu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Absolute configuration; Chiral Lewis acid; Enantioselective reaction; Radical mediated reduction

Indexed keywords

ALKYL GROUP; COUMARIN DERIVATIVE; IODINE DERIVATIVE; MAGNESIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0033588317     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00584-0     Document Type: Article

References (36)

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18. For enantioselective radical-mediated reductions of haloesters, see: Blumenstein, M.; Schwarzkopf, K.; Metzger, J. O. Angew. Chem. Int. Ed. Engl. 1997, 36, 235-236; Schwarzkopf, K.; Blumenstein, M.; Hayen, A.; Metzger, J. O. Eur. J. Org. Chem. 1998, 177-181. For enantioselective radical-mediated reductions of haloketone, see: Nanni, D.; Curran, D. P. Tetrahedron: Asymmetry 1996, 7, 2417-2422.
19. For enantioselective radical-mediated reductions of haloesters, see: Blumenstein, M.; Schwarzkopf, K.; Metzger, J. O. Angew. Chem. Int. Ed. Engl. 1997, 36, 235-236; Schwarzkopf, K.; Blumenstein, M.; Hayen, A.; Metzger, J. O. Eur. J. Org. Chem. 1998, 177-181. For enantioselective radical-mediated reductions of haloketone, see: Nanni, D.; Curran, D. P. Tetrahedron: Asymmetry 1996, 7, 2417-2422.
20. Haque, M. B.; Roberts, B. P. Tetrahedron Lett. 1996, 37, 9123-9126.
21. A part of this paper has been reported as a communication, see ref. 2. Preparation and enantioselective allylation of α-alkyl-α-iododihydrocoumarins 1 have been reported, see ref. 3j and 3k.
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25. Colombo, L.; Gennari, C.; Poli, G.; Scolastico, C. Tetrahedron 1982, 38, 2725-2727.
26. It is reported that ether moieties in α-halo-β-alkoxy esters coordinate to Lewis acids, see: Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Homer, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701-9702. Recent reports on the diastereoselective radical reactions of α-halo-β-alkoxy esters and effects of Lewis acids, see: Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. J. Am. Chem. Soc. 1996, 118, 12528-12535; Guindon, Y.; Liu, Z.; Jung, G. J. Am Chem. Soc. 1997, 119, 9289-9290; Guindon, Y.; Jung, G.; Guérin, B.; Ogilvie, W. W. Synlett 1998, 213-220; Guindon, Y.; Rancourt, J. J. Org. Chem. 1998, 63, 6554-6565 and references cited therein. There is also a report that α-alkoxymethyl-α-iodolactones seem to be a monodentate ligand to a Lewis acid, see: ref. 3j.
27. It is reported that ether moieties in α-halo-β-alkoxy esters coordinate to Lewis acids, see: Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Homer, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701-9702. Recent reports on the diastereoselective radical reactions of α-halo-β-alkoxy esters and effects of Lewis acids, see: Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. J. Am. Chem. Soc. 1996, 118, 12528-12535; Guindon, Y.; Liu, Z.; Jung, G. J. Am Chem. Soc. 1997, 119, 9289-9290; Guindon, Y.; Jung, G.; Guérin, B.; Ogilvie, W. W. Synlett 1998, 213-220; Guindon, Y.; Rancourt, J. J. Org. Chem. 1998, 63, 6554-6565 and references cited therein. There is also a report that α-alkoxymethyl-α-iodolactones seem to be a monodentate ligand to a Lewis acid, see: ref. 3j.
28. It is reported that ether moieties in α-halo-β-alkoxy esters coordinate to Lewis acids, see: Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Homer, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701-9702. Recent reports on the diastereoselective radical reactions of α-halo-β-alkoxy esters and effects of Lewis acids, see: Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. J. Am. Chem. Soc. 1996, 118, 12528-12535; Guindon, Y.; Liu, Z.; Jung, G. J. Am Chem. Soc. 1997, 119, 9289-9290; Guindon, Y.; Jung, G.; Guérin, B.; Ogilvie, W. W. Synlett 1998, 213-220; Guindon, Y.; Rancourt, J. J. Org. Chem. 1998, 63, 6554-6565 and references cited therein. There is also a report that α-alkoxymethyl-α-iodolactones seem to be a monodentate ligand to a Lewis acid, see: ref. 3j.
29. It is reported that ether moieties in α-halo-β-alkoxy esters coordinate to Lewis acids, see: Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Homer, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701-9702. Recent reports on the diastereoselective radical reactions of α-halo-β-alkoxy esters and effects of Lewis acids, see: Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. J. Am. Chem. Soc. 1996, 118, 12528-12535; Guindon, Y.; Liu, Z.; Jung, G. J. Am Chem. Soc. 1997, 119, 9289-9290; Guindon, Y.; Jung, G.; Guérin, B.; Ogilvie, W. W. Synlett 1998, 213-220; Guindon, Y.; Rancourt, J. J. Org. Chem. 1998, 63, 6554-6565 and references cited therein. There is also a report that α-alkoxymethyl-α-iodolactones seem to be a monodentate ligand to a Lewis acid, see: ref. 3j.
30. It is reported that ether moieties in α-halo-β-alkoxy esters coordinate to Lewis acids, see: Guindon, Y.; Lavallée, J.-F.; Llinas-Brunet, M.; Homer, G.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 9701-9702. Recent reports on the diastereoselective radical reactions of α-halo-β-alkoxy esters and effects of Lewis acids, see: Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. J. Am. Chem. Soc. 1996, 118, 12528-12535; Guindon, Y.; Liu, Z.; Jung, G. J. Am Chem. Soc. 1997, 119, 9289-9290; Guindon, Y.; Jung, G.; Guérin, B.; Ogilvie, W. W. Synlett 1998, 213-220; Guindon, Y.; Rancourt, J. J. Org. Chem. 1998, 63, 6554-6565 and references cited therein. There is also a report that α-alkoxymethyl-α-iodolactones seem to be a monodentate ligand to a Lewis acid, see: ref. 3j.
31. Other Lewis acids for radical initiator, see: Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421-422 and references cited therein.
32. 2 are used in the enantioselective radical-mediated reactions, see: ref. 3d, 3g-i.
33. 3 did not proceed smoothly.
34. The determination of the absolute configuration of a has been reported, see: Murakata, M.; Tsutsui, H.; Hoshino, O. Heterocycles 1997, 46, 517-522.
35. 1H NMR spectrum of the crude product. (formula presented)
36. Lopez, R. M.; Hays, D. S.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 6949-6950.