(1S,4R)-2-(4-Methoxybenzoyl)bicyclo[2.2.2]octa-2,5-diene

 

(1S,4R)-2-(4-Methoxybenzoyl)bicyclo[2.2.2]octa-2,5-diene (3a) Yellow liquid (25.2 mg, 95% yield):

1H NMR (300 MHz, CDCl3)   1.39 (s, 4H, alkyl), 3.77-3.80 (m, 1H, alkyl), 3.85 (s, 3H, OMe), 4.36 (d, J = 5.4 Hz, 1H, alkyl), 6.36 (dd, J = 6.0, 6.0 Hz, 1H, vinyl), 6.46 (dd, J = 6.0, 6.0 Hz, 1H, vinyl), 6.88-6.91 (m, 3H, vinyl + arom.), 7.67 (d, J = 8.3 Hz, 2H, arom.);

13C{1H} NMR (75 MHz, CDCl3)  = 24.7, 24.8, 37.1, 38.2, 55.4, 113.3, 130.8, 131.5, 133.2, 135.1, 146.5, 147.7, 162.6, 192.3;

HRMS (ESI-TOF) m/z calculated for C16H16NaO2 [M+Na]+ 263.1048, found 263.1036;

FT-IR (neat, cm-1 ) 1033, 1174, 1255, 1354, 1600, 1637, 1730, 2870, 2957, 3054.

Optical Rotation: []D 26 +39.9 (c 2.52, CHCl3) for an enantiomerically enriched sample of 94% ee.

HPLC analysis (column, CHIRALPAK AD-3, hexane/2-propanol = 98/2, flow rate 1.0 mL/min, 20 C, detection UV 250 nm light); tR of major-isomer 20.7

Org. Lett., 2018, 20 (23), pp 7353–7357

DOI: 10.1021/acs.orglett.8b02263

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(1S,4R)-2-(4-Methoxybenzoyl)bicyclo[2.2.2]octa-2,5-diene

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