Alkenyl and aryl boronates - Mild nucleophiles for the stereoselective formation of functionalized N-heterocycles

Journal of the American Chemical Society

Volumn 121, Issue 21, 1999, Pages 5075-5076

  Batey, Robert A ^a   MacKay, D Bruce ^a   Santhakumar, V ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALKENYL GROUP; AUSTRALINE; BORONIC ACID DERIVATIVE; CASTANOSPERMINE; HETEROCYCLIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRROLIDINE DERIVATIVE; RETRONECINE; SWAINSONINE;

ARTICLE; CATALYSIS; COMPLEX FORMATION; CYCLIZATION; DERIVATIZATION; DIASTEREOISOMER; ESTERIFICATION; HYDROGENATION; MOLECULAR INTERACTION; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033516314     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983801z     Document Type: Article

References (53)

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34. For alkenylcopper reagents see ref 3d, and: (a) Germon, C.; Alexakis, A.; Normant, J. F. Synthesis 1984, 40-43. (b) Thaning, M.; Wistrand, L.-G. Acta Chem. Scand. 1992, 46, 194-199. (c) McClure, K. F.; Renold, P.; Kemp, D. S. J. Org. Chem. 1995, 60, 454-457. (d) Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251-7264. For alkenylsilanes, see: (e) Angst, C. Pure Appl. Chem. 1987, 59, 373-380.
35. For alkenylcopper reagents see ref 3d, and: (a) Germon, C.; Alexakis, A.; Normant, J. F. Synthesis 1984, 40-43. (b) Thaning, M.; Wistrand, L.-G. Acta Chem. Scand. 1992, 46, 194-199. (c) McClure, K. F.; Renold, P.; Kemp, D. S. J. Org. Chem. 1995, 60, 454-457. (d) Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251-7264. For alkenylsilanes, see: (e) Angst, C. Pure Appl. Chem. 1987, 59, 373-380.
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44. During the course of this study Correia and co-workers reported this dihydroxylation reaction. Asymmetric dihydroxylation and asymmetric epoxidation/hydrolysis reactions gave low to moderate enantioselectivity, see: Sugisaki, C. H.; Carroll, P. J.; Correia, C. R. D. Tetrahedron Lett. 1998, 39, 3413-3416.
45. The diastereomer of 2a was prepared via Mitsonobu reaction (see Supporting Information), and was not found in crude reaction mixtures.
46. A crystal structure was obtained of (2R*,3R*)-3-hydroxy-2-phenylpyrrolidine (the pyrrolidine derived from CBZ deprotectipn of phenyl adduct 2e: see Supporting Information). The authors have deposited atomic coordinates for this compound with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
47. For previous syntheses of 1-hydroxyindolizidine, see: (a) Aaron, H. S.; Rader, C. P.; Wicks, G. E., Jr. J. Org. Chem. 1966, 31, 3502-3507. (b) Sibi, M. P.; Christensen, J. W. Tetrahedron Lett. 1990, 31, 5689. (c) Harris, C. M.; Schneider, M. J.; Ungemach, F. S.; Hill, J. E.; Harris, T. M. J. Am. Chem. Soc. 1988, 110, 940. (d) Harris, C. M.; Harris, T. M. Tetrahedron Lett. 1987, 28, 2559-2562. (e) Takahata, H.; Tajima, M.; Banba, Y.; Mosome, T. Chem. Pharm. Bull. Jpn. 1989, 37, 2550.
48. For previous syntheses of 1-hydroxyindolizidine, see: (a) Aaron, H. S.; Rader, C. P.; Wicks, G. E., Jr. J. Org. Chem. 1966, 31, 3502-3507. (b) Sibi, M. P.; Christensen, J. W. Tetrahedron Lett. 1990, 31, 5689. (c) Harris, C. M.; Schneider, M. J.; Ungemach, F. S.; Hill, J. E.; Harris, T. M. J. Am. Chem. Soc. 1988, 110, 940. (d) Harris, C. M.; Harris, T. M. Tetrahedron Lett. 1987, 28, 2559-2562. (e) Takahata, H.; Tajima, M.; Banba, Y.; Mosome, T. Chem. Pharm. Bull. Jpn. 1989, 37, 2550.
49. For previous syntheses of 1-hydroxyindolizidine, see: (a) Aaron, H. S.; Rader, C. P.; Wicks, G. E., Jr. J. Org. Chem. 1966, 31, 3502-3507. (b) Sibi, M. P.; Christensen, J. W. Tetrahedron Lett. 1990, 31, 5689. (c) Harris, C. M.; Schneider, M. J.; Ungemach, F. S.; Hill, J. E.; Harris, T. M. J. Am. Chem. Soc. 1988, 110, 940. (d) Harris, C. M.; Harris, T. M. Tetrahedron Lett. 1987, 28, 2559-2562. (e) Takahata, H.; Tajima, M.; Banba, Y.; Mosome, T. Chem. Pharm. Bull. Jpn. 1989, 37, 2550.
50. For previous syntheses of 1-hydroxyindolizidine, see: (a) Aaron, H. S.; Rader, C. P.; Wicks, G. E., Jr. J. Org. Chem. 1966, 31, 3502-3507. (b) Sibi, M. P.; Christensen, J. W. Tetrahedron Lett. 1990, 31, 5689. (c) Harris, C. M.; Schneider, M. J.; Ungemach, F. S.; Hill, J. E.; Harris, T. M. J. Am. Chem. Soc. 1988, 110, 940. (d) Harris, C. M.; Harris, T. M. Tetrahedron Lett. 1987, 28, 2559-2562. (e) Takahata, H.; Tajima, M.; Banba, Y.; Mosome, T. Chem. Pharm. Bull. Jpn. 1989, 37, 2550.
51. For previous syntheses of 1-hydroxyindolizidine, see: (a) Aaron, H. S.; Rader, C. P.; Wicks, G. E., Jr. J. Org. Chem. 1966, 31, 3502-3507. (b) Sibi, M. P.; Christensen, J. W. Tetrahedron Lett. 1990, 31, 5689. (c) Harris, C. M.; Schneider, M. J.; Ungemach, F. S.; Hill, J. E.; Harris, T. M. J. Am. Chem. Soc. 1988, 110, 940. (d) Harris, C. M.; Harris, T. M. Tetrahedron Lett. 1987, 28, 2559-2562. (e) Takahata, H.; Tajima, M.; Banba, Y.; Mosome, T. Chem. Pharm. Bull. Jpn. 1989, 37, 2550.
52. Protection of the alcohol as its TBS ether facilitated boronate synthesis.
53. For the nucleophilic addition of allenylboronic acid to a β-hydroxy ketone, possibly involving hydroxyl mediated delivery, see: Ikeda, N.; Omori, K.; Yamamoto, H. Tetrahedron Lett. 1986, 27, 1175-1178.