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DOI: 10.1055/s-2006-950293
Copper(I) Chloride Mediated Cyclization of Optically Active 2,3-Allenoic Acids or 1:1 Salts of Optically Active 2,3-Allenoic Acids with Chiral Amines
Publication History
Publication Date:
09 October 2006 (online)
Abstract
Copper(I) chloride mediated cyclization of optically active 2,3-allenoic acids or 1:1 salts of optically active 2,3-allenoic acids with chiral amines was developed. The reaction of optically active 2,3-allenoic acids in methanol requires only a catalytic amount of copper(I) chloride, while the reaction of the 1:1 salts of optically active 2,3-allenoic acids with chiral amines needs one equivalent of copper(I) chloride and should be carried out in dichloromethane to ensure high efficiency of chirality transfer.
Key words
chirality transfer - cyclization - copper(I) chloride - amines - 2,3-allenoic acids
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References
Crystal data for compound (R)-(+)-2e: C13H13BrO2, M = 281.14, monoclinic, space group P2 (1), Mo Kα, final R indices [I > 2σ(I)], R1 = 0.0657, wR2 = 0.1570, a = 4.3321 (19) Å, b = 10.916 (5) Å, c = 13.117 (6) Å, α = 90°, β = 92.942 (7)°, γ = 90°, V = 619.5 (5) Å3, T = 293 (2) K, Z = 2, reflections collected/unique: 3518:2213 (R int = 0.1593), no observation [I > 2σ(I)] 957, parameters 155; CCDC 602980 contains the data.