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

Fingerprint

Bearings (structural)
Lewis Bases
Acetals
Aldehydes
Ions

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Enantio- and Diastereoselective, Lewis Base Catalyzed, Cascade Sulfenoacetalization of Alkenyl Aldehydes. / Matviitsuk, Anastassia; Denmark, Scott E.

In: Angewandte Chemie - International Edition, Vol. 58, No. 36, 01.01.2019, p. 12486-12490.

Research output: Contribution to journalArticle

@article{c9c9b8312c6444bcaf25557d10e11f1e,
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 = "Lewis base catalysis, carbonyl nucleophiles, isochromans, sulfenoacetalization, thiiranium ions",
author = "Anastassia Matviitsuk and Denmark, {Scott E.}",
year = "2019",
month = "1",
day = "1",
doi = "10.1002/anie.201906535",
language = "English (US)",
volume = "58",
pages = "12486--12490",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "36",

}

TY - JOUR

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 - Lewis base catalysis

KW - carbonyl nucleophiles

KW - isochromans

KW - sulfenoacetalization

KW - thiiranium ions

UR - http://www.scopus.com/inward/record.url?scp=85070062134&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85070062134&partnerID=8YFLogxK

U2 - 10.1002/anie.201906535

DO - 10.1002/anie.201906535

M3 - Article

C2 - 31295383

AN - SCOPUS:85070062134

VL - 58

SP - 12486

EP - 12490

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 36

ER -