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Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 10, 1997, Pages 1299-1302

Synthesis of monohydroxylated 2-azabicyclo[2.2.1]heptan-3-ones

(7) Palmer, Christopher F a Webb, Ben a Broad, Susan b Casson, Sharon b McCague, Raymond a Willetts, Andrew J b Roberts, Stanley M b

a Chiroscience Ltd (United Kingdom)

b NONE

Author keywords

[No Author keywords available]

Indexed keywords

CARBOCYCLIC NUCLEOSIDE; NORBORNANE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031579957 PISSN: 0960894X EISSN: None Source Type: Journal
DOI: 10.1016/S0960-894X(97)00217-5 Document Type: Article

Times cited : (16)

References (24)

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2
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7
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20
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- Representative 300MHz 1H NMR data for the 5-exo, 5-endo, and 6-exo silyl ethers (2-4, R1 = Bn, R2 = tBDMS) is shown below:- 5-exo ( 2 ) 4.22 (1H, ddd, J5-endo-6-endo 6.6Hz, J5-endo-7-anti 1.3Hz, J5-endo-6-exo 2.2Hz, H-5endo), 2.02 (12H, app dd J6-endo-6-exo 13Hz, J6-endo-5-endo 6.6Hz, H-6endo), 1.94 (2H, m, H-7anti, H-7syn), 1.46 (1H, ddd, J6-exo-6-endo 13Hz, J6-exo-5-endo 2.2Hz, J6exo-4 2.1Hz, H-6exo). 5-endo ( 3 ) δ (CDCl3) 4.52 (2H, m including J5-exo-6-exo 8Hz, J5-exo-4 4.2Hz and J5-exo-6-endo 2.9Hz, H-5exo and CH2Ph), 1.94 (1H, ddd, J6-exo-6-endo 13Hz, J6-exo-5-exo 8Hz and J6-exo-1 2.4Hz, H-6exo); 6-exo ( 4 ) (see also ) 3.76 6-endo-5-endo 6.6Hz, J6-endo-5-exo 2.2Hz, H-6endo), 2.00 (1H, dd, J5-endo-5-exo 13Hz, J5-endo-6-endo 6.6Hz, H-5exo), 1.50 (1H, ddd, J6-exo-6-endo 13Hz, 5exo-H-4 4.0Hz, J5exo-6-endo 2.2Hz, H-6exo).
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