Stereoselective α-amidoalkylation reactions of phenylglycinol-derived bicyclic lactams

Tetrahedron Asymmetry

Volumn 14, Issue 12, 2003, Pages 1679-1683

  Amat, Mercedes ^a   Escolano, Carmen ^a   Llor, Núria ^a   Huguet, Marta ^a   Pérez, Maria ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLTRIMETHYLSILANE; GLYCINE DERIVATIVE; INDOLE; LACTAM DERIVATIVE; PHENYLGLYCINOL; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHIRALITY; GRIGNARD REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0037867664     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00250-7     Document Type: Article

References (23)

1. For reviews, see: (a) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503-9569; (b) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1-8; (c) Groaning, M. D.; Meyers, A. I. Tetrahedron 2000, 56, 9843-9873.
2. For reviews, see: (a) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503-9569; (b) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1-8; (c) Groaning, M. D.; Meyers, A. I. Tetrahedron 2000, 56, 9843-9873.
3. For reviews, see: (a) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503-9569; (b) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1-8; (c) Groaning, M. D.; Meyers, A. I. Tetrahedron 2000, 56, 9843-9873.
4. Amat M., Llor N., Bosch J. Tetrahedron Lett. 35:1994;2223-2226.
5. Amat M., Bosch J., Hidalgo J., Cantó M., Pérez M., Llor N., Molins E., Miravitlles C., Orozco M., Luque J. J. Org. Chem. 65:2000;3074-3084.
6. Amat M., Llor N., Escolano C., Huguet M., Pérez M., Molins E., Bosch J. Tetrahedron: Asymmetry. 13:2003;293-295.
7. For other reports on the preparation of cis-1 and trans-1, see: (a) Royer, J.; Husson, H.-P. Heterocycles 1993, 36, 1493-1496; (b) Micouin, L.; Quirion, J.-C.; Husson, H.-P. Synth. Commun. 1996, 26, 1605-1611.
8. For other reports on the preparation of cis-1 and trans-1, see: (a) Royer, J.; Husson, H.-P. Heterocycles 1993, 36, 1493-1496; (b) Micouin, L.; Quirion, J.-C.; Husson, H.-P. Synth. Commun. 1996, 26, 1605-1611.
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10. Amat M., Llor N., Hidalgo J., Escolano C., Bosch J. J. Org. Chem. 67:2003;1919-1928 See also Ref. 2b.
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12. For related approaches, involving the reductive ring-opening of phenylgycinol-derived 8a-substituted bicyclic δ-lactams, see: (a) Munchhof, M. J.; Meyers, A. I. J. Org. Chem. 1995, 60, 7084-7085; (b) Fréville, S.; Célérier, J. P.; Thuy, V. M.; Lhommet, G. Tetrahedron: Asymmetry 1995, 6, 2651-2654; (c) Amat, M.; Cantó, M.; Llor, N.; Bosch, J. Chem. Commun. 2002, 526-527.
13. For related approaches, involving the reductive ring-opening of phenylgycinol-derived 8a-substituted bicyclic δ-lactams, see: (a) Munchhof, M. J.; Meyers, A. I. J. Org. Chem. 1995, 60, 7084-7085; (b) Fréville, S.; Célérier, J. P.; Thuy, V. M.; Lhommet, G. Tetrahedron: Asymmetry 1995, 6, 2651-2654; (c) Amat, M.; Cantó, M.; Llor, N.; Bosch, J. Chem. Commun. 2002, 526-527.
14. For related approaches, involving the reductive ring-opening of phenylgycinol-derived 8a-substituted bicyclic δ-lactams, see: (a) Munchhof, M. J.; Meyers, A. I. J. Org. Chem. 1995, 60, 7084-7085; (b) Fréville, S.; Célérier, J. P.; Thuy, V. M.; Lhommet, G. Tetrahedron: Asymmetry 1995, 6, 2651-2654; (c) Amat, M.; Cantó, M.; Llor, N.; Bosch, J. Chem. Commun. 2002, 526-527.
15. For a discussion on the stereoselectivity of allyltrimethylsilane α-amidoalkylations of related (R)-phenylglycinol- or (S)-1-phenylethylamine-derived δ- and γ-lactams, see: (a) Polniaszek, R. P.; Belmont, S. E.; Alvarez, R. J. Org. Chem. 1990, 55, 215-223; (b) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535; (c) Burgess, L. E.; Meyers, A. I. J. Am. Chem. Soc. 1991, 113, 9858-9859.
16. For a discussion on the stereoselectivity of allyltrimethylsilane α-amidoalkylations of related (R)-phenylglycinol- or (S)-1-phenylethylamine-derived δ- and γ-lactams, see: (a) Polniaszek, R. P.; Belmont, S. E.; Alvarez, R. J. Org. Chem. 1990, 55, 215-223; (b) Kiguchi, T.; Nakazono, Y.; Kotera, S.; Ninomiya, I.; Naito, T. Heterocycles 1990, 31, 1525-1535; (c) Burgess, L. E.; Meyers, A. I. J. Am. Chem. Soc. 1991, 113, 9858-9859.
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18. Iminosugars as Glycosidase Inhibitors. Nojirimicin and Beyond; Stütz, A. E., Ed.; Wiley-VCH: Weinheim, 1999.
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23. Amat M., Pérez M., Llor N., Bosch J. Org. Lett. 4:2002;2787-2790 See also Ref. 2b.