Application of Mosher's method for absolute configuration assignment and resolution of 2-hydroxypyrrolizidinones

Chirality

Volumn 17, Issue 3, 2005, Pages 149-153

  Cordero, Franca M ^a   Pisaneschi, Federica ^a   Salvati, Maria ^a   Valenza, Silvia ^a   Faggi, Cristina ^a   Brandi, Alberto ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Chirality; Heterocycles; MTPA ester; NMR spectroscopy; X ray crystallography

Indexed keywords

2 HYDROXYPYRROLIZIDINONE DERIVATIVE; ALPHA METHOXY ALPHA TRIFLUOROMETHYLPHENYLACETYL CHLORIDE; FLUOROFORM; PHENYLACETIC ACID DERIVATIVE; PYRROLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; MOSHER METHOD; PRIORITY JOURNAL; RACEMIC MIXTURE; STEREOISOMERISM;

CRYSTALLOGRAPHY; CRYSTALLOGRAPHY, X-RAY; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PHENYLACETATES; PYRROLIDINONES; STEREOISOMERISM;

EID: 14844313690     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20139     Document Type: Article

References (9)

1. Dale JA, Mosher HS. Nuclear magnetic resonance enantiomer reagents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α- trifluoromethylphenylacetate (MTPA) esters. J Am Chem Soc 1973;95:512-519.
2. Ohtani I, Kusumi T, Kashman Y, Kakisawa H. High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids. J Am Chem Soc 1991;113:4092-4096.
3. Seco JM, Quinoa E, Riguera R. A practical guide for the assignment of the absolute configuration of alcohols, amines and carboxylic acids by NMR. Tetrahedron: Asymmetry 2001;12:2915-2925.
4. For a recent review, see: Seco JM, Quinoa E, Riguera R. The assignment of absolute configuration by NMR. Chem Rev 2004;104: 17-117.
5. Seco JM, Quinoa E, Riguera R. The assignment of absolute configurations by NMR of arylmethoxyacetate derivatives: is this methodology being correctly used? Tetrahedron: Asymmetry 2000;11: 2781-2791.
6. Cordero FM, Valenza S, Machetti F, Brandi A. Design and synthesis of a new bicyclic dipeptide isostere. Chem Commun 2001:1590-1591.
7. Cordero FM, Pisaneschi F, Meschini Batista K, Valenza S, Machetti F, Brandi A. A new bicyclic dipeptide isostere with pyrrolizidinone skeleton. J Org Chem (in press).
8. Dale JA, Dull DL, Mosher HS. α-Methoxy-α- trifluoromethylphenyl-acetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines. J Org Chem 1969;34:2543-2549.
9. Crystallographic data of 3a and 3b have been deposited at CCDC and allocated with the deposition numbers CCDC 239906 for 3a and CCDC 166488 for 3b. Copies of the data can be obtained, free of charge, via http://www.ccdc.cam.ac. uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Center, 12, Union Road, Cambridge CB2 1EZ, UK; fax +44-1223-336033: or deposit@ccdc.cam.ac.uk).