(R)- and (S)-Proline-Derived Chiral Phosphoramides as Organo­catalysts for the Enantiodivergent Aldol Reaction of Isatins with Cyclohexanone in the Presence of Water

Carlos Cruz-Hernández; Perla E. Hernández-González; Eusebio Juaristi

doi:10.1055/s-0036-1591916

Synthesis, Table of Contents

Synthesis 2018; 50(09): 1827-1840
DOI: 10.1055/s-0036-1591916

paper

(R)- and (S)-Proline-Derived Chiral Phosphoramides as Organocatalysts for the Enantiodivergent Aldol Reaction of Isatins with Cyclohexanone in the Presence of Water

Carlos Cruz-Hernández

^aDepartamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida IPN 2508, 07360 Ciudad de México, Mexico

,

Perla E. Hernández-González

^aDepartamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida IPN 2508, 07360 Ciudad de México, Mexico

,

Eusebio Juaristi *

^aDepartamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida IPN 2508, 07360 Ciudad de México, Mexico

^bEl Colegio Nacional, Luis González Obregón 23, Centro Histórico, 06020 Ciudad de México, Mexico Email: juaristi@relaq.mx

› Author Affiliations

Abstract

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Abstract

Novel organocatalysts derived from (R)- and (S)-proline and incorporating a chiral phosphoramide fragment were rationally designed and subsequently synthesized. These chiral compounds catalyze the enantioselective aldol addition reaction of cyclohexanone to prochiral isatins in the presence of water. These observations are particularly relevant since reports of asymmetric aldol reactions between cyclohexanone and isatins catalyzed by chiral secondary amines remain scarce, with primary amines being the most studied and successful catalysts. The present report includes a thorough evaluation of the new bifunctional catalysts that actually give rise to either enantiomer of the chiral product by proper selection of the configuration of the proline moiety.

Key words

asymmetric organocatalysis - dual activation - hydrophobic interactions - Brønsted acids - Lewis bases

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References

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33 Crystal data for (1S,2S,1′S,2′S)-1 (CCDC 1589107): C₂₂H₃₂Cl₂N₂, orthorhombic, P2₁2₁2₁; a = 12.130(2) Å, b = 12.166(2) Å, c = 13.935(3) Å; α = 90°, β = 90°, γ = 90°; V = 2056.4(7) Å³; z = 4, z′ = 1; R ₁ = 4.23%.
34 Crystal data for (1R,2R,1′R,2′R)-2 (CCDC 1589128): C₂₂H₂₈ClN₂OP, tetragonal, P4₁; a = 9.337(4) Å, b = 9.337 Å, c = 24.805(15) Å; α = 90°, β = 90°, γ = 90°; V = 2162.5(13) Å³; z = 4, z′ = 1; R ₁ = 3.5%.
35 Crystal data for (1S,2S,1′R,2′R)-3 (CCDC 1589095): C₂₂H₂₈N₅OP, orthorhombic, P2₁2₁2₁; a = 7.5054(3) Å, b = 8.6800(4) Å, c = 34.1605(5) Å; α = 90°, β = 90°, γ = 90°; V = 2225.45(17) Å³; z = 4, z′ = 1; R ₁ = 4.27%.
36 Crystal data for (1R,2R,1′S,2′S)-3 (CCDC 1589094): C₂₂H₂₈N₅OP, orthorhombic, P2₁2₁2₁; a = 7.4759(4) Å, b = 8.6939(4) Å, c = 34.2042(17) Å; α = 90°, β = 90°, γ = 90°; V = 2223.09(19) Å³; z = 4, z′ = 1; R ₁ = 5.56%.
37 Crystal data for (1S,2S,1′R,2′R)-4 (CCDC 1589105): C₂₂H₃₀N₃OP, monoclinic, P2₁; a = 12.2137(2) Å, b = 7.6245(1) Å, c = 12.6593(3) Å; α = 90°, β = 115.379(1)°, γ = 90°; V = 1065.11(4) Å³; z = 2, z′ = 1; R ₁ = 4.26%.
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Supplementary Material

Supporting Information

(R)- and (S)-Proline-Derived Chiral Phosphoramides as Organo­catalysts for the Enantiodivergent Aldol Reaction of Isatins with Cyclohexanone in the Presence of Water

(R)- and (S)-Proline-Derived Chiral Phosphoramides as Organocatalysts for the Enantiodivergent Aldol Reaction of Isatins with Cyclohexanone in the Presence of Water