Enantio- and Diastereoselective, Lewis Base Catalyzed, Cascade Sulfenoacetalization of Alkenyl Aldehydes

Anastassia Matviitsuk, Scott E. Denmark

Research output: Contribution to journalArticle

Abstract

A catalytic, enantio-, and diastereoselective formation of sulfenyl acetals bearing multiple stereogenic centers is reported. Alkenyl aldehydes undergo a chiral thiiranium ion initiated cascade starting with intramolecular capture by a formyl group and termination by capture with HFIP solvent. This method provides a one-pot synthesis of dihydropyran and 1,3-disubstituted isochroman acetals in good to excellent yield and with high levels of diastereo- (up to >99:1 dr) and enantiocontrol (up to 99:1 er).

Original languageEnglish (US)
Pages (from-to)12486-12490
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number36
DOIs
StatePublished - Jan 1 2019

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Keywords

  • Lewis base catalysis
  • carbonyl nucleophiles
  • isochromans
  • sulfenoacetalization
  • thiiranium ions

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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