Enantioselective Synthesis of Siloxyallenes from Alkynoylsilanes by Reduction and a Brook Rearrangement and Their Subsequent Trapping in a [4+2] Cycloaddition

Abstract

Two flavors of selectivity: An enantioselective Meerwein–Ponndorf–Verley-type reduction of alkynoylsilanes by a chiral lithium amide followed by a Brook rearrangement and SE2′ electrophilic substitution provides the title compounds in a one-pot process. In the case of enynoylsilanes, the generated vinylallenes undergo in situ [4+2] cycloaddition to afford highly functionalized polycyclic compounds with unusual facial selectivity. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.