Abstract
Oxo esters with pyrrolidine and tetrahydrofuran rings were converted
into optically active isobenzofuran and isoindole derivatives. The
key step of the sequence was a copper-catalyzed asymmetric Michael
reaction with methyl vinyl ketone and enamines prepared
from the oxo esters and l -valine diethylamide.
The chiral auxiliary was cleaved from the products during workup
and 1,5-diketones with a quaternary stereocenter are obtained with
97-99% ee. Subsequent
annulation reactions were achieved in two steps via the intermediate
aldol products.
Key words
tetrahydrofurans - pyrrolidines - isoindoles - isobenzofurans - chirality - Michael
addition - quaternary stereocenters
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CCDC 785562 contains the supplementary
crystallographic data for this paper. These data can be obtained
free of charge via www.ccdc.cam.ac.uk, or by emailing data_request@ccdc.cam.ac.uk,
or by contacting The Cambridge Crystallographic Data Centre, 12
Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033.
