2017
DOI: 10.1021/jacs.7b05802
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Helical Oligourea Foldamers as Powerful Hydrogen Bonding Catalysts for Enantioselective C–C Bond-Forming Reactions

Abstract: Substantial progress has been made toward the development of metal-free catalysts of enantioselective transformations, yet the discovery of organic catalysts effective at low catalyst loadings remains a major challenge. Here we report a novel synergistic catalyst combination system consisting of a peptide-inspired chiral helical (thio)urea oligomer and a simple tertiary amine that is able to promote the Michael reaction between enolizable carbonyl compounds and nitroolefins with excellent enantioselectivities … Show more

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Cited by 88 publications
(64 citation statements)
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“…[24] The chiral acetal moiety in the (R,R)-Ac 4 c 3BD was changeable and may also be used for low pH-triggerings tructural changes. [25] Therefore, precisely elucidated helical secondary structures may be invaluable for designing organo-catalysts, [26] cell-penetrating peptides, [27] and targetbinding peptides. [24] .…”
mentioning
confidence: 99%
“…[24] The chiral acetal moiety in the (R,R)-Ac 4 c 3BD was changeable and may also be used for low pH-triggerings tructural changes. [25] Therefore, precisely elucidated helical secondary structures may be invaluable for designing organo-catalysts, [26] cell-penetrating peptides, [27] and targetbinding peptides. [24] .…”
mentioning
confidence: 99%
“…The hierarchical structure of biomacromolecules has long inspired chemists to design abiotic foldamers, oligomers that adopt well-defined conformations because of noncovalent interactions. [1][2][3][4][5] Foldamers exhibiting molecular recognition, [6][7][8][9] catalysis, [10,11] interesting electronic properties, [12][13][14] self-assembly, [15] and biological activity [16][17][18] are now known. Ultimately, the goal is to complement biological systems, achieving analogous structural sophistication, and thus function, but using structural motifs with distinct properties.…”
Section: Introductionmentioning
confidence: 99%
“…15 Nevertheless over the years the involvement of organic uorine in HB in large number of molecules including foldamers have been reported. [16][17][18][19][20][21][22] The studies report that the inter-or intra-molecular HB of the type X-H/F-C (X ¼ O, N) plays a signicant role in the dynamics as well as the functionalities of the drugs 23 viz., dipole-dipole interaction, HB and steric hinderance.…”
Section: Introductionmentioning
confidence: 99%