4,4-Dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-2-en-1-one → (S)-2-tert-butoxy-2-(1-(3,3-dimethyl-6-oxocyclohex-1-enyl)-3-methylnaphthalen-2-yl)acetic acid

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Reaction Steps

(S)-2-tert-Butoxy-2-(1-(3,3-dimethyl-6-oxocyclohex-1-enyl)-3-methylnaphthalen-2-yl)acetic acid (11) was prepared following the procedure to make (S)-2-tert-butoxy-2-(1-cyclohexenyl-3-methylnaphthalen-2-yl)acetic acid of Example 6 except that 4,4-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-2-enone was used instead of cyclohexenylboronic acid. Atropisomers were separated by flash column chromatography. 1H-NMR: 400 MHz, (CD3OD) δ: 7.72 (d, J=8.2 Hz, 1H), 7.59 (s,1H), 7.39 (m, 2H), 7.37 (m, 1H), 7.02 (s, 1H), 5.42 (s,1H), 2.82 (m, 1H), 2.67 (m, 1H), 2.58 (s, 3H), 2.18 (m, 2H), 1.38 (s, 6H), 1.08 (s, 9H). LCMS-ESI+ (m/z): [M−H]− calcd for C25H29O4: 393.50. found: 393.0.

Provenance & Evidence