Tetrahydrofuran → HCID 66746618, compound

Reaction equation

O[B:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[O:3]1.C[C@@:17]1([OH:27])[C@H:22]([OH:23])[CH2:21][C@@H:20]2[CH2:24][C@H:18]1[C:19]2([CH3:26])[CH3:25].[CH2:28]1COCC1>>[OH:3][CH:4]([CH2:5][CH2:6][CH2:7][B:2]1[O:23][C@:22]2([CH3:28])[C@@H:17]([C@@H:18]3[CH2:24][C@H:20]([CH2:21]2)[C:19]3([CH3:25])[CH3:26])[O:27]1)[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 10219606(+)-Pinanediol

HCID 66747249HCID 66747249, compound

Product 1

HCID 66746618HCID 66746618, compoundYield 71.9%

Procedure

To a solution of tert-butyl 2-(2-hydroxy-1,2-oxaborinan-6-yl)acetate XLVIII (641 mg, 3.00 mmol) in THF (20 mL) was added (1S,2S,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol (509 mg, 3 mol) at room temperature. The reaction mixture was stirred for 16 h and concentrated under vacuum. The residue was purified by column chromatography (100% hexane→40% EtOAc/hexane) on silica gel to give tert-butyl 3-hydroxy-6-[(1R,2R,6S,8R)-6,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]hexanoate XLIX (790 mg, 2.16 mmol, 71.9% yield).