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One‐Step Synthesis of Strained Bicyclic Carboxylic and Boronic Amino Esters via Ruthenium‐Catalysed Tandem Carbene Addition/Cyclopropanation of Enynes
Author(s) -
Bray Chloé VovardLe,
Klein Hubert,
Dixneuf Pierre H.,
Macé Aurélie,
Berrée Fabienne,
Carboni Bertrand,
Dérien Sylvie
Publication year - 2012
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.201200117
Subject(s) - chemistry , cyclopropanation , ruthenium , carbene , diazo , bicyclic molecule , combinatorial chemistry , tandem , catalysis , organic chemistry , medicinal chemistry , materials science , composite material
The reaction of 1,6‐ and 1,7‐enynes, derived from carboxylic and boronic amino acids, with diazo compounds in the presence of the (cyclooctadiene)(pentamethylcyclopentadiene)ruthenium chloride complex [RuCl(cod)(C 5 Me 5 )] catalyst leads to the formation of strained bicyclic proline or homoproline derivatives in good yields. This catalytic transformation proceeds under mild conditions, in one step from easily accessible enynes and was applied to various protecting groups. High stereoselectivities for the created alkenyl chain and excellent diastereoselectivities for proline derivatives were obtained.