Rhodium‐Catalyzed Cycloisomerization Involving Cyclopropenes: Efficient Stereoselective Synthesis of Medium‐Sized Heterocyclic Scaffolds | Zendy

Miege Frédéric | Zendy; Meyer Christophe | Zendy; Cossy Janine | Zendy

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Rhodium‐Catalyzed Cycloisomerization Involving Cyclopropenes: Efficient Stereoselective Synthesis of Medium‐Sized Heterocyclic Scaffolds

Author(s) -

Miege Frédéric,

Meyer Christophe,

Cossy Janine

Publication year - 2011

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201101220

Subject(s) - carbenoid , cycloisomerization , cyclopropanation , intramolecular force , rhodium , stereoselectivity , ring (chemistry) , chemistry , alkene , diazo , combinatorial chemistry , stereochemistry , bicyclic molecule , catalysis , medicinal chemistry , organic chemistry

A happy medium : The title reaction of cyclopropenyl carbinols and carbinylamines gives carbo‐ and heterocycles with a [6.1.0] bicyclic ring fused to an aromatic ring (see scheme, Alloc=allyloxycarbonyl, Boc= tert ‐butyloxycarbonyl). These reactions are the first examples of the formation of medium‐sized rings by the intramolecular cyclopropanation of an alkene with a donor‐substituted rhodium carbenoid, which is not generated from a diazo compound.

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