The exo-selectivity of the new non-natural chiral auxiliary (+)-(1R,endo)-2-benzonorbornenol in an asymmetric aza-Diels-Alder reaction

Tetrahedron Letters

Volumn 44, Issue 3, 2003, Pages 431-433

  Fernández, Franco ^a   García Mera, Xerardo ^a   Rodríguez Borges, José Enrique ^b   Vale, María Luisa C ^b  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITY OF PORTO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; GLYOXYLIC ACID; IMINE;

ARTICLE; CHIRALITY; DIASTEREOISOMER; DIELS ALDER REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

BETULACEAE;

EID: 0037433970     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02599-6     Document Type: Article

References (21)

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13. Unpublished results.
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18. 3): 36.28 (C-3′), 43.83 (C-4′), 48.23 (C-1′), 48.55 (C-9′), 74.68 (C-2′), 120.77 (C-5′), 123.95 (C-8′), 126.02 (C-7′), 126.69 (C-6′), 128.95 (C-2), 130.73 (C-3), 142.98 (C-8a), 148.60 (C-4a), 166.58 (C(O)).
19. 4) and concentrated, affording a yellow oil that upon filtration through a short column of silica gel using 3:1 hexane:EtOAc as eluent afforded 4 as a mixture of the glyoxylate and its hydrate that was used without further purification. Yield 1.92 g (91%).
20. exo-H), 6.05-6.08 (d×d, 1H, J=5.50, 1.92 Hz, 5-H), 6.25-6.28 (d×d, 1H, J=5.50, 3.35 Hz, 6-H), 6.76-7.28 (m, 9H, ArH).
21. 2OH), 127.55 (C-4′), 128.80 (C-2′+C-6′), 129.43 (C-3′+C-5′), 132.71 (C-5), 138.27 (C-6), 140.11 (C-1′).