9-anthrylmethoxyacetic acid esterification shifts-correlation with the absolute stereochemistry of secondary alcohols

Tetrahedron

Volumn 55, Issue 2, 1999, Pages 569-584

  Seco, José Manuel ^a   Quiñoá, Emilio ^a   Riguera, Ricardo ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Alcohols; Configuration; NMR; Stereochemistry

Indexed keywords

ALCOHOL; METHOXYACETIC ACID; PROTON;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; ESTERIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033534444     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01055-2     Document Type: Article

References (11)

1. Seco JM, Latypov ShK, Quiñoá E, Riguera R. Tetrahedron 1997; 53: 8541-8564 and references therein.
2. For a review see: Uray G in Houben-Weyl Methods in Organic Chemistry, Vol 1 (Helchen G, Hoffmann RW, Mulzer J. and Schaumann E, Ed), Thieme, Stuttgart - New York, 1996, p. 253.
3. Trost BM, Bunt RC, Pulley ShR. J. Org. Chem. 1994; 92: 4583-4585.
4. Seco, JM, Latypov ShK, Quiñoá E, Riguera R. J. Org. Chem. 1997; 62: 7569-7574 and references therein.
5. Latypov ShK, Ferreiro MJ, Quiñoá E, Riguera R. J. Am. Chem. Soc. 1998; 120: 4741-4751.
6. Nagai Y, Kusumi T. Tetrahedron Lett. 1994; 36: 1853-1856.
7. Fukusi Y, Shigematsu K, Mizutani J, Tahara S. Tetrahedron Lett. 1996; 37: 5737-4740.
8. Ferreiro MJ, Latypov ShK, Quiñoá E, Riguera R. Tetrahedron: Asymmetry 1997; 8: 1015-1018.
9. Latypov ShK, Seco JM, Quiñoá E, Riguera R. J. Am. Chem. Soc. 1998; 120: 877-882.
10. Lenis LA, Ferreiro MJ, Debitus C, Jiménez C, Quiñoá E, Riguera R. Tetrahedron 1998; 54: 5385-5406.
11. 1H NMR spectra of (R)- and (S)-9AMA esters of (R)-2-pentanol and (+)-menthol were taken and found to be identical to those of their enantiomeric pairs.