ChemInform Abstract: Highly Enantioselective Asymmetric Michael Addition Reactions with New Chiral Multisite Phase‐Transfer Catalysts.

Sivamani, Jayaraman; Duraimurugan, Kumaraguru; Arockiam, Jesin Beneto; Paulpandian, Subha; Balasaravanan, Rajendiran; Siva, Ayyanar

doi:10.1002/chin.201502081

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“…Since the 1990s, asymmetric PTC has emerged as a topic of scientific interest. Consequently, different chiral catalysts derived from cinchona alkaloids, amino acids, and 1,1 -bi-2-naphthol (BINOL) alongside macrocyclic compounds have been synthesized and applied [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Methyl 4,6-Di-O-ethyl-α-d-glucopyranoside-Based Azacrown Ethers and Their Effects in Asymmetric Reactions

et al. 2021

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Carbohydrate-based crown ethers have been reported to be able to generate asymmetric induction in certain reactions. Previously, it was proved that the monosaccharide unit, the anomeric substituent, and the sidearm could influence the catalytic activity of the monoaza-15-crown-5 macrocycles derived from sugars. In order to gain information about the effect of the flexibility, 4,6-di-O-ethyl-glucoside-based crown compounds were synthesized, and their efficiency was compared to the 4,6-O-benzylidene analogues. It was found that the absence of the two-ring annulation has a negative effect on the enantioselectivity in liquid-liquid two-phase reactions: in the Darzens condensation of 2-chloroacetophenone and in the epoxidation of chalcone. The same trend was observed in the solid-liquid phase Michael addition of diethyl acetamidomalonate. Surprisingly, in the solid-liquid phase cyclopropanation of benzylidenemalononitrile, one of the new catalysts was highly enantioselective (99% ee).

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Section: Introductionmentioning

confidence: 99%

Synthesis of Methyl 4,6-Di-O-ethyl-α-d-glucopyranoside-Based Azacrown Ethers and Their Effects in Asymmetric Reactions

et al. 2021

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ChemInform Abstract: Highly Enantioselective Asymmetric Michael Addition Reactions with New Chiral Multisite Phase‐Transfer Catalysts.

Abstract: Catalysts. -The synthesis of the catalysts (I) is described. The O-Bn analogue of the catalyst delivers comparable results. -(JAYARAMAN, S.; KUMARAGURU, D.; AROCKIAM, J. B.; PAULPANDIAN, S.; RAJENDIRAN, B.; SIVA*, A.; Synlett 25 (2014) 12, 1685-1691, http://dx.

Cited by 1 publication

References 1 publication

Synthesis of Methyl 4,6-Di-O-ethyl-α-d-glucopyranoside-Based Azacrown Ethers and Their Effects in Asymmetric Reactions

Synthesis of Methyl 4,6-Di-O-ethyl-α-d-glucopyranoside-Based Azacrown Ethers and Their Effects in Asymmetric Reactions

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