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Volumn 5, Issue 22, 2003, Pages 4235-4238

Iterative Organometallic Addition to Chiral Hydroxylated Cyclic Nitrones: Highly Stereoselective Syntheses of α,α′- and α,α-Substituted Hydroxypyrrolidines

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AMINO ACID; NITRONE DERIVATIVE; PROLINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

EID: 0344944860     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035798g     Document Type: Article
Times cited : (86)

References (39)
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    • Disubstituted pyrroline N-oxides have been subjected to iterative additions for the synthesis of nitroxides. See for example: (a) Keana, J. F.; Lee, T. D.; Bernard, E. M. J. Am. Chem. Soc. 1976, 98, 3052-3053. (b) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Gautier-Luneau, I.; Pierre, J.-L. J. Org. Chem. 1997, 62, 9385-9388.
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    • A synthesis of (-)-codonopsinine by alkylation of a L-xylose-derived nitrone has been recently reported: see ref 2b. For other syntheses of 13 and 14, see: (a) Haddad, M.; Larchevêque, M. Synlett 2003, 274-276. (b) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039-3042. (c) Yoda, H.; Nakajima, T.; Takabe, K. Tetrahedron Lett. 1996, 37, 5531-5534. (d) Wang, C.-L. J.; Calabrese, J. C. J. Org. Chem. 1991, 56, 4341-4343. (e) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 1956-1962.
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    • A synthesis of (-)-codonopsinine by alkylation of a L-xylose-derived nitrone has been recently reported: see ref 2b. For other syntheses of 13 and 14, see: (a) Haddad, M.; Larchevêque, M. Synlett 2003, 274-276. (b) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039-3042. (c) Yoda, H.; Nakajima, T.; Takabe, K. Tetrahedron Lett. 1996, 37, 5531-5534. (d) Wang, C.-L. J.; Calabrese, J. C. J. Org. Chem. 1991, 56, 4341-4343. (e) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 1956-1962.
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    • A synthesis of (-)-codonopsinine by alkylation of a L-xylose-derived nitrone has been recently reported: see ref 2b. For other syntheses of 13 and 14, see: (a) Haddad, M.; Larchevêque, M. Synlett 2003, 274-276. (b) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039-3042. (c) Yoda, H.; Nakajima, T.; Takabe, K. Tetrahedron Lett. 1996, 37, 5531-5534. (d) Wang, C.-L. J.; Calabrese, J. C. J. Org. Chem. 1991, 56, 4341-4343. (e) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 1956-1962.
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    • A synthesis of (-)-codonopsinine by alkylation of a L-xylose-derived nitrone has been recently reported: see ref 2b. For other syntheses of 13 and 14, see: (a) Haddad, M.; Larchevêque, M. Synlett 2003, 274-276. (b) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039-3042. (c) Yoda, H.; Nakajima, T.; Takabe, K. Tetrahedron Lett. 1996, 37, 5531-5534. (d) Wang, C.-L. J.; Calabrese, J. C. J. Org. Chem. 1991, 56, 4341-4343. (e) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 1956-1962.
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    • A synthesis of (-)-codonopsinine by alkylation of a L-xylose-derived nitrone has been recently reported: see ref 2b. For other syntheses of 13 and 14, see: (a) Haddad, M.; Larchevêque, M. Synlett 2003, 274-276. (b) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039-3042. (c) Yoda, H.; Nakajima, T.; Takabe, K. Tetrahedron Lett. 1996, 37, 5531-5534. (d) Wang, C.-L. J.; Calabrese, J. C. J. Org. Chem. 1991, 56, 4341-4343. (e) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 1956-1962.
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