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One‐Step Ruthenium‐Catalysed Transformation of 1,7‐Enynes into Strained Bicyclic Amino Esters
Author(s) -
Moulin Solenne,
Roisnel Thierry,
Dérien Sylvie
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600896
Subject(s) - chemistry , bicyclic molecule , steric effects , diazo , stereoselectivity , ruthenium , pipecolic acid , catalysis , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , amino acid , biochemistry
The reaction of 1,7‐enynes, synthesised from α‐amino acids, carried out with diazo compounds in the presence of the Cp*RuCl(cod) catalyst allowed the one‐step preparation of various strained bicyclic pipecolic acid derivatives in good yields under mild conditions. The stereoselectivity of the created double bond depends on the nature of the diazoalkane, and the diastereoselectivity arises essentially from steric factors.