Gold‐Catalyzed Stereoselective Domino Cyclization/Alkynylation of  N ‐Propargylcarboxamides with Benziodoxole Reagents for the Synthesis of Alkynyloxazolines | Zendy

Zhao Ximei | Zendy; Tian Bing | Zendy; Yang Yangyang | Zendy; Si Xiaojia | Zendy; Mulks Florian F. | Zendy; Rudolph Matthias | Zendy; Rominger Frank | Zendy; Hashmi A. Stephen K. | Zendy

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Gold‐Catalyzed Stereoselective Domino Cyclization/Alkynylation of N ‐Propargylcarboxamides with Benziodoxole Reagents for the Synthesis of Alkynyloxazolines

Author(s) -

Zhao Ximei,

Tian Bing,

Yang Yangyang,

Si Xiaojia,

Mulks Florian F.,

Rudolph Matthias,

Rominger Frank,

Hashmi A. Stephen K.

Publication year - 2019

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201900264

Subject(s) - stereoselectivity , chemistry , domino , alkynylation , reagent , combinatorial chemistry , catalysis , substrate (aquarium) , cascade , selectivity , cascade reaction , stereochemistry , organic chemistry , oceanography , chromatography , geology

A concise and highly stereoselective synthesis of alkynyloxazolines via a gold‐catalyzed domino cyclization‐alkynylation cascade of N ‐propargylcarboxamides with benziodoxole reagents is reported. This new protocol, which represents an attractive alternative to two step sequences based on Sonagashira couplings, offers a broad substrate scope, excellent functional group tolerance, and perfect stereoselectivity. A comparison of the computed energies of the isomers of the product suggests kinetic control as the cause of the observed selectivity.

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