The Grob/Eschenmoser fragmentation of cycloalkanones bearing ß-electron withdrawing groups: a general strategy to acyclic synthetic intermediates.
Org Biomol Chem
; 9(3): 783-92, 2011 Feb 07.
Article
in En
| MEDLINE
| ID: mdl-21103511
ABSTRACT
Introduction of a ß-electron withdrawing group to cycloalkanones allows facile C-C bond fragmentation. The reaction has been demonstrated with a large range of ring sizes, bearing various leaving and electron withdrawing groups, and using a variety of nitrogen and oxygen containing nucleophiles (>30 examples). The application of fragmentation products to the preparation of substituted γ-lactones has been demonstrated. Mechanistic studies are reported which are suggestive of a Grob/Eschenmoser type reaction.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Org Biomol Chem
Journal subject:
BIOQUIMICA
/
QUIMICA
Year:
2011
Document type:
Article
Affiliation country:
Australia