The use of 1-amino-2-phenyl-1-cyclohexanecarboxylic acids as chiral auxiliaries in asymmetric Diels-Alder reactions

Tetrahedron

Volumn 52, Issue 13, 1996, Pages 4839-4848

  Avenoza, Alberto ^a   Cativiela, Carlos ^b   París, Miguel ^a   Peregrina, Jesús M ^a  

^a UNIVERSITY OF LA RIOJA   (Spain)

^b UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANECARBOXYLIC ACID DERIVATIVE; NORBORNANE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

BETULACEAE;

EID: 0029989560     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00155-X     Document Type: Article

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16. tbutylmethyl ether (80:20). Flow rate: 2.0 mL/min. Retention times: (2a or 2b) = 6.83 min, (3a or 4b) = 5.49 min, (4a or 3b) = 4.57 min, (5a + 6a or 5b + 6b) = 2.85 min. (2c or 2d) = 6.86 min, (3c or 4d) = 5.52 min, (4c or 3d) = 4.61 min, (5c + 6c or 5d + 6d) = 2.90 min.
17. 5 vinylic protons (δ, ppm): 5.83 (3a or 4b), 5.76 (4a or 3b), 6.06 (5a + 6a or 5b + 6b). 5.72 (3c or 4d), 5.76 (4c or 3d), 6.04 (5c + 6c or 5d + 6d).
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25. 3: C 71.72, H 7.70, N 4.65 found: C 71.85, H 7.77, N 4.60.
26. 1H-NMR spectra (δ, ppm): 3.04 and 3.05 (12a and 13a). 3.11 and 3.12 (10a and 11a).
27. 2a); 3.51(s, 3H, COOMe).