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Synthesis 2011(6): 895-900
DOI: 10.1055/s-0030-1258419
DOI: 10.1055/s-0030-1258419
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Enantioselective Synthesis of Hexahydroisobenzofuran and Hexahydroisoindole Derivatives with Quaternary Stereocenters
Further Information
Publication History
Received
3 November 2010
Publication Date:
01 March 2011 (online)


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