4,4,5,5-Tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane → HCID 117902617, compound

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Reaction Steps

The title compound is synthesized and purified analogously to 4b [except allylboronic acid pinacol ester 1b (32 μL, 0.15 mmol) is used as the nucleophile instead of 1a], affording 4m (34.4 mg, 0.0952 mmol, 95% yield) as a white solid. The analytical data are fully consistent with those reported previously.13 1H NMR (400 MHz, CDCl3): δ 7.86-7.80 (2H, m), 7.76-7.70 (2H, m), 7.50-7.46 (1H, m), 7.44-7.38 (3H, m), 7.29-7.17 (7H, m), 4.78 (1H, s), 4.69 (1H, s), 4.40 (1H, dddd, J=16.4, 16.4, 8.4, 8.4 Hz), 3.32 (1H, br dd, J=8.0, 6.0 Hz), 2.62 (1H, dd, J=13.6, 7.2 Hz), 2.53 (1H, dd, J=14.0, 7.2 Hz), 1.58 (3H, s); HRMS Calcd for C23H25NOP [M+H]+: 362.16738. Found: 362.16649. [α]20D=+39 (c=1.2, CHCl3) for a 97.5:2.5 er sample. The enantiomeric purity was determined by HPLC analysis in comparison with authentic racemic material (Chiracel OD-H, 92:8 hexanes:i-PrOH, 0.8 mL/min, 220 nm): tR of 4m: 11 min (major) and 14 min (minor).

Provenance & Evidence