Control of Six Contiguous Stereocenters in an Asymmetric Organocatalytic One‐Pot Michael/Michael/Aldol Addition Sequence
Advanced Synthesis & CatalysisPublished 9 May 2012
Dieter Enders, Gregor Urbanietz, Elisa Cassens‐Sasse, Sebastian Keeß, Gerhard Raabe
Citations41
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TL;DR
The one-pot protocol follows a Michael/Michael/aldol addition sequence and affords the highly substituted cyclohexanes in moderate to very good yields, diastereomeric ratios of dr>95:5 and excellent enantioselectivities of 91–99% ee.
Abstract
Abstract The asymmetric organocatalytic one‐pot synthesis of polyfunctionalized cyclohexanes is described. Starting from β‐keto esters, nitroalkenes and α,β‐unstaturated aldehydes and employing a bifunctional norephedrine‐based thiourea catalyst, six contiguous stereocenters including one quarternary center are generated. The one‐pot protocol follows a Michael/Michael/aldol addition sequence and affords the highly substituted cyclohexanes in moderate to very good yields (22–70%), diastereomeric ratios of dr >95:5 and excellent enantioselectivities of 91–99% ee .
Keywords
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