Enantioselective Synthesis of Cyclopentene Carbaldehydes by a Direct Multicatalytic Cascade Sequence: Carbocyclization of Aldehydes with Alkynes

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Abstract

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A multicatalytic, asymmetric cascade reaction sequence of α,β-unsaturated aldehydes with alkyne-tethered nucleophiles has been developed. Organocatalytic iminium–enamine catalysis combined with Lewis acid alkyne activation gave cyclopentene carbaldehyde products in good yields and excellent stereoselectivities (see scheme). To highlight the potential of the sequence, a key structure for the preparation of a fusicoccane diterpenoid analogue was synthesized.

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