[CH2:1](B([C@H]1C[C@H]2C[C@H](C2(C)C)[C@@H]1C)[C@H]1C[C@H]2C[C@H](C2(C)C)[C@@H]1C)[CH:2]=[CH2:3].[Cl:25][C:26]1[CH:31]=[CH:30][N:29]=[C:28]([CH:32]=[O:33])[C:27]=1[F:34].[OH-].[Li+].OO.[OH-].[Na+]>CCCCC.C1COCC1.CCOC(C)=O.CO>[Cl:25][C:26]1[CH:31]=[CH:30][N:29]=[C:28]([C@H:32]([OH:33])[CH2:3][CH:2]=[CH2:1])[C:27]=1[F:34]A solution of 1 M allylbis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane in pentane in anhydrous THF (10 mL) was cooled to −78° C. To the solution was added 4-chloro-3-fluoropicolinaldehyde (0.5 g, 3.13 mmol) in 10 mL of THF dropwise for 20 min. The resulting solution was stirred for additional 1 h. To the mixture was added MeOH (1 mL), followed addition of lithium hydroxide (0.300 g, 12.54 mmol), hydrogen peroxide (0.384 mL, 12.54 mmol) and 10 mL of 1 N NaOH. The content was allowed to warm up to rt and stirred for 1 h. The reaction mixture was diluted with EtOAc, washed with brine (2×20 mL), dried over Na2SO4, concentrated and purified by silica gel chromatography to provide (R)-1-(4-chloro-3-fluoropyridin-2-yl)but-3-en-1-ol (0.54 g, 85%). MS (ESI) m/z: 202.1 (M+H)+.
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