- Single-Handed Helical Poly(quinoxaline-2,3-diyl)s Bearing Achiral 4-Aminopyrid-3-yl Pendants as Highly Enantioselective, Reusable Chiral Nucleophilic Organocatalysts in the Steglich Reaction
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Helically chiral poly(quinoxaline-2,3-diyl)s bearing 4-aminopyrid-3-yl pendants were synthesized as new helical-polymer-based chiral nucleophilic organocatalysts. The obtained chiral nucleophilic polymer catalysts exhibited high catalytic activity, enantioselectivity, and reusability in asymmetric Steglich rearrangement of oxazolyl carbonate to C-carboxyazlactone. The polyquinoxaline-based, helically chiral DMAP catalyst mediated intramolecular acyl transfer selectively, by contrast with known small-molecule-based chiral organocatalysts, which also mediate intermolecular acyl transfers.
- Yamamoto, Takeshi,Murakami, Ryo,Suginome, Michinori
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supporting information
p. 2557 - 2560
(2017/03/01)
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- Concise synthesis, preparative resolution, absolute configuration determination, and applications of an atropisomeric biaryl catalyst for asymmetric acylation
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A new three-step synthesis and resolution of nucleophilic catalyst 1 suitable for large-scale preparation has been developed, and this catalyst has been shown to be effective for the kinetic resolution and asymmetric desymmetrization of a range of sec-alcohol substrates.
- Spivey, Alan C.,Zhu, Fujiang,Mitchell, Mark B.,Davey, Stephen G.,Jarvest, Richard L.
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p. 7379 - 7385
(2007/10/03)
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