Catalytic ring expansion of vinyl oxetanes: Asymmetric synthesis of dihydropyrans using chiral counterion catalysis

Boying Guo; Gregg Schwarzwalder; Jon T. Njardarson

doi:10.1002/anie.201201367

Catalytic ring expansion of vinyl oxetanes: Asymmetric synthesis of dihydropyrans using chiral counterion catalysis

Boying Guo, Gregg Schwarzwalder, Jon T. Njardarson

Research output: Contribution to journal › Article › peer-review

70 Scopus citations

Abstract

Acid Showdown! The first catalytic ring expansion of vinyl oxetanes to 3,6-dihydro-2H-pyrans is described. Copper(II) triflate emerged as the best catalyst for this new transformation, which has broad scope as demonstrated by the eighteen examples included. The symmetric vinyl oxetane substrate can be asymmetrically desymmetrized when using either chiral Lewis or Brønsted acids as catalysts.

Original language	English (US)
Pages (from-to)	5675-5678
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	23
DOIs	https://doi.org/10.1002/anie.201201367
State	Published - Jun 4 2012
Externally published	Yes

Keywords

chiral counterions
copper
homogeneous catalysis
ring expansion
vinyl oxetanes

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201201367

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abstract = "Acid Showdown! The first catalytic ring expansion of vinyl oxetanes to 3,6-dihydro-2H-pyrans is described. Copper(II) triflate emerged as the best catalyst for this new transformation, which has broad scope as demonstrated by the eighteen examples included. The symmetric vinyl oxetane substrate can be asymmetrically desymmetrized when using either chiral Lewis or Br{\o}nsted acids as catalysts.",

keywords = "chiral counterions, copper, homogeneous catalysis, ring expansion, vinyl oxetanes",

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AU - Schwarzwalder, Gregg

AU - Njardarson, Jon T.

PY - 2012/6/4

Y1 - 2012/6/4

N2 - Acid Showdown! The first catalytic ring expansion of vinyl oxetanes to 3,6-dihydro-2H-pyrans is described. Copper(II) triflate emerged as the best catalyst for this new transformation, which has broad scope as demonstrated by the eighteen examples included. The symmetric vinyl oxetane substrate can be asymmetrically desymmetrized when using either chiral Lewis or Brønsted acids as catalysts.

AB - Acid Showdown! The first catalytic ring expansion of vinyl oxetanes to 3,6-dihydro-2H-pyrans is described. Copper(II) triflate emerged as the best catalyst for this new transformation, which has broad scope as demonstrated by the eighteen examples included. The symmetric vinyl oxetane substrate can be asymmetrically desymmetrized when using either chiral Lewis or Brønsted acids as catalysts.

KW - chiral counterions

KW - copper

KW - homogeneous catalysis

KW - ring expansion

KW - vinyl oxetanes

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Catalytic ring expansion of vinyl oxetanes: Asymmetric synthesis of dihydropyrans using chiral counterion catalysis

Abstract

Keywords

ASJC Scopus subject areas

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