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

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 stereose...

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Bibliographic Details
Published in:Chemistry : a European journal 2010-02, Vol.16 (6), p.1750-1753
Main Authors: Jensen, Kim L., Franke, Patrick T., Arróniz, Carlos, Kobbelgaard, Sara, Jørgensen, Karl Anker
Format: Article
Language:English
Subjects:
Activation
Aldehydes
Aldehydes - chemistry
Alkynes
Alkynes - chemistry
Asymmetry
cascade reactions
Catalysis
Chemistry
Cyclization
Cyclopentanes - chemical synthesis
Cyclopentene
cyclopentenes
Lewis acid
Lewis acids
Nucleophiles
organocatalysis
Stereoisomerism
Synthesis
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Summary: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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200903405