Synthesis of Substituted Cyclic Ethers from Halo Ketones and Halo Aldehydes by Palladium-Catalyzed Coupling with Organotin Reagents

I. Pri-Bar, P. S. Pearlman, J. K. Stille

Research output: Contribution to journalArticlepeer-review

39 Scopus citations

Abstract

Received February 25, 1983 The palladium-catalyzed reaction of a variety of halo ketones or halo aldehydes with acetonyl- and allyltin reagents gives cyclic ethers in good yields. Oxiranes, oxetanes, and tetrahydrofurans can be obtained under mild reaction conditions. The use of palladium catalyst containing chiral monophosphine ligands gave a small enantiomeric excess (up to 19%) of a chiral oxirane from an a-halo ketone. The allyl- and acetonyloxirane products tend to undergo further transformations in prolonged reactions: allyloxiranes rearrange to a-allyl aldehydes and acetonyloxiranes dehydrate to give substituted furans. The mechanism of the reaction appears to involve addition of the organotin ligand to the carbonyl, followed by palladium(II)-catalyzed cyclization of the tin alkoxides.

Original languageEnglish
Pages (from-to)4629-4634
Number of pages6
JournalJournal of Organic Chemistry
Volume48
Issue number24
DOIs
StatePublished - 1 Jan 1983
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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