trans-2-Phenoxycyclohexan-1-OL as New Chiral Auxiliary: Synthesis of Chiral α-Hydroxy Acids

References

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• A solution of trans-2-phenoxycyclohexan-1-ol (2) (7.68g,40mM), benzoylformic acid (6.75g, 45mM), and p-toluenesulfonic acid (0.3g,1.57mM) in 100 mL of benzene was heated under reflux with azeotropic removal of water for 3h. Usual work up followed by crystallization from pet.ether provided 72% (9.33g) of pure 3. m.p. 75–76°C 13C NMR (CDC13) δ 186.89, 163.83, 157.53, 134.77, 132.24, 129.94, 129.59, 128.77, 121.36, 116.12, 77.41, 76.30, 29.76, 29.59, 23.23, 22.88. 1H NMR (CDC13) δ 8.0–6.8 (m, 10H), 5.32 (m, 1H), 4.28 (m, 1H), 2.4–1.2 (m, 8H). IR(CHC13) 1730, 1690 cm−1. Analysis calcd for C20H20O4: C, 74.05; H, 6.215; found C, 74.10; H,6.215. [α]D 24 -50.43 (c 1.125 Acetone)
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