Evaluation of a Pseudoephedrine Linker for Asymmetric Alkylations on Solid Phase

Organic Letters

Volumn 4, Issue 26, 2002, Pages 4583-4585

  Hutchison, Panee C ^a   Heightman, Tom D ^b   Procter, David J ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038145590     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0268788     Document Type: Article

References (35)

1. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
2. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
3. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
4. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
5. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
6. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
7. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
8. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
9. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
10. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
11. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
12. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
13. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
14. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
15. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
16. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
17. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
18. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
19. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
20. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
21. Carbohydrate-based auxiliaries: (a) Kawana, M.; Emoto, S. Tetrahedron Lett. 1972, 48, 4855. Kawana, M.; Emoto, S. Bull. Chem. Soc. Jpn. 1974, 47, 160. (b) Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431. Chiral amines: (c) Worster, P. M.; McArthur, C. R.; Leznoff, C. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 221. McArthur, C. R.; Worster, P. M.; Jiang, J.-L.; Leznoff, C. C. Can. J. Chem. 1982, 60, 1836. Evans oxazolidinones: (d) Allin, S. M.; Shuttleworth, S. J. Tetrahedron Lett. 1996, 37, 8023. (e) Burgess, K.; Lim, D. Chem. Commun. 1997, 785. (f) Purandare, A. V.; Natarajan, S. Tetrahedron Lett. 1997, 38, 8777. (g) Phoon, C. W.; Abell, C. Tetrahedron Lett. 1998, 39, 2655. (h) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39, 4935. (i) Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron Lett. 2000, 41, 1265. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Seneci, P. Tetrahedron 2001, 57, 8313. Desimoni, G.; Faita, G.; Galbiati, A.; Pasini, D.; Quadrelli, P.; Rancati, F. Tetrahedron: Asymmetry 2002, 13, 333. Pyrrolidine-based auxiliaries: (j) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. Moon, H.-s.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915. Oppolzer's camphorsultam: (k) Miyabe, H.; Konishi, C.; Naito, T. Org. Lett. 2000, 2, 1443. Oxazolines: (l) Colwell, A. R.; Duckwall, L. R.; Brooks, R.; McManus, S. P. J. Org. Chem. 1981, 46, 3097. Hydrazine auxiliaries: (m) Enders, D.; Kirchhoff, J. H.; Köbberling, J.; Peiffer, T. H. Org. Lett. 2001, 3, 1241. Alcohol auxiliary: (n) Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859. Sulfinamide auxiliary: (o) Dragoli, D. R.; Burdett, M. T.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127. α-Hydroxyvaline auxiliary: (p) Savinov, S. N.; Austin, D. J. Org. Lett. 2002, 4, 1419.
22. Bew, S. P.; Bull, S. D.; Davies, S. G. Tetrahedron Lett. 2000, 41, 7577.
23. McKerlie, F.; Procter, D. J.; Wynne, G. Chem. Commun. 2002, 584.
24. (a) Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488.
25. (b) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656.
26. (c) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496.
27. (d) Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428.
28. (e) Myers, A. G.; Schnider, P.; Kwon, S.; Kung, D. W. J. Org. Chem. 1999, 64, 3322.
29. Näslund, J.; Welch, C. J. Tetrahedron: Asymmetry 1991, 2, 1123. In our hands, solution-phase benzylation of pseudoephedrine under these conditions was found to give less than 5% N-benzyl pseudoephedrine. Thus, similar high selectivity for O-alkylation is expected in the immobilization step.
30. For a discussion, see ref 4c.
31. For the R = H series, diastereoselectivities were determined by conversion of 6 into the corresponding TMS ether and analysis by GCMS. For the R = Bn series, the diastereoisomeric purity of 5 was obtained indirectly from the enantiomeric excess of 7.
32. In some IR spectra, extremely faint ester carbonyl stretches could also be seen. This is in agreement with previous observations regarding high selectivity in the O-alkylation of pseudoephedrine (see ref 5).
33. Myers, A. G.; Yang, B. H.; Kopecky, D. J. Tetrahedron Lett. 1996, 37, 3623.
34. 19F NMR.
35. 19F NMR (see ref 4c). Enantiomeric excess of 11g was determined by chiral HPLC.