Remote substituent effect favoring the formation of syn-adducts in the chelation controlled radical reactions of γ-benzyloxy-α-methylenecarboxylic acid esters

Tetrahedron

Volumn 59, Issue 20, 2003, Pages 3649-3663

  Nagano, Hajime ^a   Ohkouchi, Hisako ^a   Yajima, Tomoko ^a  

^a OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

1,3 asymmetric induction; CONFLEX PM3; Lewis acid; Radical reaction; Remote substituent effect

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; GAMMA BENZYLOXY ALPHA METHYLENE ESTER; IODINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASSAY; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHELATION; CYCLOADDITION; DIASTEREOISOMER; ENERGY; GEOMETRY; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; RADICAL REACTION; STEREOCHEMISTRY;

EID: 0038741725     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00421-6     Document Type: Article

References (42)

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38. It should be emphasized that enantiomerically pure α-hydroxy and α-amino aldehydes, the starting materials for the preparation of chiral γ-benzyloxy-α-methylenecarboxylic acids esters, are easily available, see: (a) Agami C., Couty F., Lequesne C. Tetrahedron Lett. 35:1994;3309-3312 (b) Cho B.T., Chun Y.S. J. Chem. Soc., Perkin Trans. 1. 1999;2095-2100. and references cited therein (c) Dondoni A., Perrone D. Synthesis. 1997;527-529 (d) Dondoni A., Perrone D. Org. Synth. 77:1999;64-77 (e) Banfi L., Guanti G., Riva R., Basso A., Calcagno E. Tetrahedron Lett. 43:2002;4067-4069.
39. It should be emphasized that enantiomerically pure α-hydroxy and α-amino aldehydes, the starting materials for the preparation of chiral γ-benzyloxy-α-methylenecarboxylic acids esters, are easily available, see: (a) Agami C., Couty F., Lequesne C. Tetrahedron Lett. 35:1994;3309-3312 (b) Cho B.T., Chun Y.S. J. Chem. Soc., Perkin Trans. 1. 1999;2095-2100. and references cited therein (c) Dondoni A., Perrone D. Synthesis. 1997;527-529 (d) Dondoni A., Perrone D. Org. Synth. 77:1999;64-77 (e) Banfi L., Guanti G., Riva R., Basso A., Calcagno E. Tetrahedron Lett. 43:2002;4067-4069.
40. It should be emphasized that enantiomerically pure α-hydroxy and α-amino aldehydes, the starting materials for the preparation of chiral γ-benzyloxy-α-methylenecarboxylic acids esters, are easily available, see: (a) Agami C., Couty F., Lequesne C. Tetrahedron Lett. 35:1994;3309-3312 (b) Cho B.T., Chun Y.S. J. Chem. Soc., Perkin Trans. 1. 1999;2095-2100. and references cited therein (c) Dondoni A., Perrone D. Synthesis. 1997;527-529 (d) Dondoni A., Perrone D. Org. Synth. 77:1999;64-77 (e) Banfi L., Guanti G., Riva R., Basso A., Calcagno E. Tetrahedron Lett. 43:2002;4067-4069.
41. It should be emphasized that enantiomerically pure α-hydroxy and α-amino aldehydes, the starting materials for the preparation of chiral γ-benzyloxy-α-methylenecarboxylic acids esters, are easily available, see: (a) Agami C., Couty F., Lequesne C. Tetrahedron Lett. 35:1994;3309-3312 (b) Cho B.T., Chun Y.S. J. Chem. Soc., Perkin Trans. 1. 1999;2095-2100. and references cited therein (c) Dondoni A., Perrone D. Synthesis. 1997;527-529 (d) Dondoni A., Perrone D. Org. Synth. 77:1999;64-77 (e) Banfi L., Guanti G., Riva R., Basso A., Calcagno E. Tetrahedron Lett. 43:2002;4067-4069.
42. It should be emphasized that enantiomerically pure α-hydroxy and α-amino aldehydes, the starting materials for the preparation of chiral γ-benzyloxy-α-methylenecarboxylic acids esters, are easily available, see: (a) Agami C., Couty F., Lequesne C. Tetrahedron Lett. 35:1994;3309-3312 (b) Cho B.T., Chun Y.S. J. Chem. Soc., Perkin Trans. 1. 1999;2095-2100. and references cited therein (c) Dondoni A., Perrone D. Synthesis. 1997;527-529 (d) Dondoni A., Perrone D. Org. Synth. 77:1999;64-77 (e) Banfi L., Guanti G., Riva R., Basso A., Calcagno E. Tetrahedron Lett. 43:2002;4067-4069.