Enantioselective Vinylogous Amination of 5-Alkyl-4-nitroisoxazoles with a Dipeptide-Based Guanidinium Phase-Transfer Catalyst | Zendy

Bo Zhu | Zendy; Richmond Lee | Zendy; Yanli Yin | Zendy; Fuyuan Li | Zendy; Michelle L. Coote | Zendy; Zhiyong Jiang | Zendy

Open Access

Enantioselective Vinylogous Amination of 5-Alkyl-4-nitroisoxazoles with a Dipeptide-Based Guanidinium Phase-Transfer Catalyst

Author(s) -

Bo Zhu,

Richmond Lee,

Yanli Yin,

Fuyuan Li,

Michelle L. Coote,

Zhiyong Jiang

Publication year - 2018

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.7b03759

Subject(s) - chemistry , enantioselective synthesis , amination , stereocenter , alkyl , catalysis , dipeptide , deprotonation , combinatorial chemistry , nucleophile , hydrogen bond , amide , organocatalysis , organic chemistry , molecule , amino acid , ion , biochemistry

An enantioselective vinylogous amination of 5-alkyl-4-nitroisoxazoles is reported. With a novel chiral dipeptide-based urea-amide-guanidinium as the phase-transfer catalyst, the reactions worked efficiently with NaOAc as the base, affording valuable and challenging-to-synthesize chiral isoxazole derivatives featuring a single stereocenter at the α-position in high yields and with excellent enantioselectivities. Theoretical studies with DFT predicted that cooperative multiple hydrogen-bonding and ion pairing interactions of a nucleophile and NaOAc with the catalyst is crucial to deprotonation by reducing their HOMO-LUMO energy gap.

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