Stereoselective Lewis acid-catalyzed α-acylvinyl additions

Troy E. Reynolds, Ashwin R. Bharadwaj, Karl A Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

46 Scopus citations

Abstract

Silyloxyallenes derived from α-hydroxypropargylsilanes undergo efficient addition to aldehydes with catalytic amounts of Lewis acids. The allenes are accessed from the corresponding propargylsilanes in a base-catalyzed 1,2-Brook rearrangement/SE2′ process. Enantioenriched propargylsilanes are synthesized by a new zinc-promoted addition of alkynes to acylsilanes in up to 74% ee. This work demonstrates that conversion to the silyloxyallenes occurs with minimal erosion in optical activity. The use of a chiral chromium(III) Lewis acid effects the catalytic asymmetric addition of racemic silyloxyallenes to aromatic aldehydes in up to 92% ee. The overall reaction is broad in scope and accommodates a wide variety of aromatic and aliphatic substituents on both the propargylsilane and aldehyde.

Original languageEnglish (US)
Pages (from-to)15382-15383
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number48
DOIs
StatePublished - Dec 6 2006

ASJC Scopus subject areas

  • Chemistry(all)

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