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Synlett 2005(10): 1609-1611
DOI: 10.1055/s-2005-869840
DOI: 10.1055/s-2005-869840
LETTER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Tetrahydrofurans through a Novel Pseudo-meso-trick
Further Information
Received
30 March 2005
Publication Date:
12 May 2005 (online)
Publication History
Publication Date:
12 May 2005 (online)
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Abstract
Diastereoselective synthesis of trisubstituted tetrahydrofuran (d-lyxo-4) from the equimolar diastereomeric mixture of d-erythro- /d -threo-1-pentenitols (1) is described. The synthesis exploits a sequence of two novel reactions: diastereospecific palladium(II)-catalyzed bicyclization of pentenitols 1 with degeneration of the allylic stereogenic center and subsequent regioselective ring-opening of bicyclic skeleton 2.
Key words
palladium - catalysis - stereoselective synthesis - cyclizations - diastereoselectivity
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