Stereospecific Rearrangement of β-Amino Alcohols Catalyzed by H₂SO₄

Abstract

Highly enantioselective rearrangement of β-amino alcohols was realized by using a catalytic amount of H₂SO₄.

Key words

amino alcohols - stereoselective synthesis - rearrangement - catalysis - chiral pool

References and Notes

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13

Typical Procedure
To a solution of β-amino alcohol 1a-j (1 mmol, 1.0 equiv) in THF (1.5 mL) at r.t. was added H₂SO₄ (3 µL, 0.05 mmol, 5 mol%) and the reaction mixture was heated at 180 °C during 2 h under microwave irradiation in a sealed tube. After addition of an aq sat. Na₂CO₃ solution, the mixture was extracted with EtOAc, dried over MgSO₄, filtered, and concentrated under reduced pressure. Purification of the residue by flash chromatography (silica gel, n-pentane-EtOAc) afforded the corresponding β-amino alcohol 2a-j.