Novel extension of Meyers' methodology: stereoselective construction of axially chiral 7,5-fused bicyclic lactams |
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Authors: | Penhoat Maël Levacher Vincent Dupas Georges |
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Institution: | Laboratoire de Chimie Organique Fine et Hétérocyclique Associé au CNRS, IRCOF-INSA, Rue Tesnières B.P 08, F-76131 Mont Saint Aignan Cédex, France. |
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Abstract: | A novel extension of Meyer's lactamization is reported for the preparation of seven-membered ring lactams 1a-d incorporating a biaryl unit. The required keto-esters 2a-c were readily accessible via the Suzuki coupling reaction. A borylation-Suzuki coupling (BSC) sequence was successfully developed for the high-yielding preparation of keto-ester 2d. Cyclization of the resulting keto-esters 2a-d or keto-acids 5a,c,d in the presence of (R)-phenylglycinol afforded the desired lactams 1a-d in high yields (72-93%) and excellent diastereoselectivities (>95%). This methodology provides a facile stereoselective access to new axially chiral bridged biaryls. |
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