Electric Literature of 871-90-9,Some common heterocyclic compound, 871-90-9, name is 8-Chlorooct-1-ene, molecular formula is C8H15Cl, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 8-Chlorooct-1-ene, its application will become more common.
Reference:
Patent; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Shi Shiliang; Cai Yuan; Yang Xintuo; Li Feng; (67 pag.)CN109776422; (2019); A;,
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