A novel asymmetric route to 2-amino-1,2,3,4-tetrahydronaphthalenes

Tetrahedron Letters

Volumn 41, Issue 17, 2000, Pages 3187-3191

  Harris, Michael C J ^a   Jackson, Mark ^a   Lennon, Ian C ^a   Ramsden, James A ^a   Samuel, Helen ^a  

^a Chirotech Technology Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 EPOXY 3 BUTENE; 2 AMINOTETRALIN; ALKENE; ALLYL COMPOUND; GLYCINE DERIVATIVE; PALLADIUM; PHTHALIMIDE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CRYSTALLIZATION; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; REACTION ANALYSIS;

EID: 0034701467     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00327-0     Document Type: Article

References (21)

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9. Determined by HPLC: Chiracel OD, UV 254 nm, 1.0 ml/min, 10% IPA, 90% heptane. RT (R)=12.8 min, RT (S)=15.9 min.
10. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545.
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15. All new compounds gave satisfactory spectral and analytical data.
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17. A cyclodehydration has been reported for 1-alkyl substituted tetralins: Kropp, P. J.; Breton, G. W.; Craig, S. L.; Crawford, S. D.; Durland Jr., W. F.; Jones III, J. E.; Raleigh, J. S. J. Org. Chem. 1995, 60, 4146.
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20. GC method, Chiralsil Dex CB column: (R)-6-methoxy-2-aminotetralin, ee>98%, compound derivatised with trifluoroacetic anhydride, 155°C for 25 mins, ramp to 200°C at 10°C/min, hold for 5 mins, RT (R)=24.0 min, RT (S)=23.5 min; (R)-2-aminotetralin, ee 97%, compound derivatised with propionic anhydride, 165°C for 25 mins, ramp to 200°C at 10°C/min, hold for 5 mins, RT (R)=24.6 min, RT (S)=23.8 min.
21. GC method, Chiraldex BTA, vinylglycinol was derivatised with acetic anhydride, 150°C for 20 mins, RT (S)=9.9 min, RT (R)=10.2 min.