Burns AR, González JS, Lam HW * University of Edinburgh, UK
Enantioselective Copper(I)-Catalyzed Borylative Aldol Cyclizations of Enone Diones.
Angew. Chem. Int. Ed. 2012;
51: 10827-10831
Key words
conjugate boration - aldol cyclization - copper - domino reaction
Significance
The formation of metal enolates allows for precise enolization, as well as potential
enantio- and diastereoselective enolization. In this report, the authors apply this
idea to a copper-catalyzed conjugate boration–aldol cyclization sequence to produce
enantioenriched decalin-, hydrindane- and diquinone-based products.
Comment
The copper–bisphosphine catalyst system developed, produces decalins as well as [5,6]-,
[6,5]-, and [5,5]-bicyclic ring products with high levels of diastereo- and enantioselectivity.
Kinetic resolution of a racemic chiral enone also afforded the cyclization product
with good diastereo- and enantioselectivity.
