A New Dual Catalytic System for Asymmetric Morita-Baylis-Hillman Reaction

Abstract

High yields and enantioselectivities up to 88% were achieved in asymmetric Morita-Baylis-Hillman reactions using a combination of chiral amino acid derived guanidines and triphenylphosphane as a novel dual catalytic system.

Key words

asymmetric catalysis - amino acids - addition reactions - stereoselective synthesis

References and Notes

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13

Typical Procedure of the MBH Reaction of Methyl Acrylate with Aldehydes Triphenylphosphine (262 mg, 1 mmol) was added to a solution of the aldehyde (1.0 mmol), methyl acrylate (300 mg, 3.0 mmol), and catalyst (0.2 mmol) in THF (1 mL) at 10 ˚C. The reaction mixture was stirred for about 36 h. After completion of the reaction (TLC check) the reaction mixture was partitioned with EtOAc (2 × 25 mL) and H₂O (2 × 25 mL). The organic phase was washed with brine (2 × 25mL), dried over Na₂SO₄, and evaporated under reduced pressure. The residue was purified by column chromatography
(n-hexane-EtOAc = 4:1).