Diastereospecific Gold(I)‐Catalyzed Cyclization Cascade for the Controlled Preparation of N‐ and N,O‐Heterocycles | Zendy

Muratore Michael E. | Zendy; Konovalov Andrey I. | Zendy; ArmengolRelats Helena | Zendy; Echavarren Antonio M. | Zendy

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Diastereospecific Gold(I)‐Catalyzed Cyclization Cascade for the Controlled Preparation of N‐ and N,O‐Heterocycles

Author(s) -

Muratore Michael E.,

Konovalov Andrey I.,

ArmengolRelats Helena,

Echavarren Antonio M.

Publication year - 2018

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201802770

Subject(s) - chemistry , cycloisomerization , oxime , enyne , catalysis , alkene , intramolecular force , carbene , moiety , cationic polymerization , medicinal chemistry , cascade , cascade reaction , diastereomer , combinatorial chemistry , stereochemistry , organic chemistry , chromatography

The reaction of oxime‐tethered 1,6‐enynes with a cationic gold(I) catalyst demonstrates a great potential for the synthesis of a range of heterocycles in a diastereospecific fashion. The control of the configuration of the oxime and the alkene of the enyne moiety is the key to selectively obtain dihydro‐1,2‐oxazines, isoxazolines or dihydropyrrole‐ N ‐oxides as single diastereoisomers. As supported by DFT calculations, these cascade reactions proceed stepwise, by the intramolecular addition of the O or N atom of the oxime onto cyclopropyl gold(I) carbene intermediates. In this study, a rare [3,3]‐sigmatropic rearrangement of nitrones is also observed.

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