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Asymmetric Hydroformylation of an Enantiomerically Pure Bicyclic Lactam: Efficient Synthesis of Functionalised Cyclopentylamines
Author(s) -
Noonan Gary M.,
Cobley Christopher J.,
Lebl Tomas,
Clarke Matthew L.
Publication year - 2010
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.201002233
Subject(s) - bicyclic molecule , hydroformylation , selectivity , lactam , ligand (biochemistry) , chemistry , combinatorial chemistry , enantiomer , stereochemistry , organic chemistry , catalysis , receptor , rhodium , biochemistry
Customising a bicycle : Rh‐catalysed asymmetric hydroformylation of a bicyclic lactam, 2‐azabicyclo‐[2.2.1]hept‐5‐en‐3‐one, was investigated. The use of a chiral diphosphite ligand, ( R , R )‐Kelliphite, enables excellent selectivity towards one regioisomer combined with excellent productivity and perfect exo selectivity. The products are versatile precursors to highly desired functionationalised cyclopentylamines (see scheme).