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)
JournalAngewandte Chemie - International Edition
DOIs
StatePublished - Jan 1 2019

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Bearings (structural)
Lewis Bases
Acetals
Aldehydes
Ions

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

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title = "Enantio- and Diastereoselective, Lewis Base Catalyzed, Cascade Sulfenoacetalization of Alkenyl Aldehydes",
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).",
keywords = "carbonyl nucleophiles, isochromans, Lewis base catalysis, sulfenoacetalization, thiiranium ions",
author = "Anastassia Matviitsuk and Denmark, {Scott E}",
year = "2019",
month = "1",
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doi = "10.1002/anie.201906535",
language = "English (US)",
journal = "Angewandte Chemie - International Edition",
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T1 - Enantio- and Diastereoselective, Lewis Base Catalyzed, Cascade Sulfenoacetalization of Alkenyl Aldehydes

AU - Matviitsuk, Anastassia

AU - Denmark, Scott E

PY - 2019/1/1

Y1 - 2019/1/1

N2 - 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).

AB - 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).

KW - carbonyl nucleophiles

KW - isochromans

KW - Lewis base catalysis

KW - sulfenoacetalization

KW - thiiranium ions

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