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

71 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

Access to Document

10.1002/anie.201201367

Cite this

@article{39b294d181ce442ea4be603eababb5f0,

title = "Catalytic ring expansion of vinyl oxetanes: Asymmetric synthesis of dihydropyrans using chiral counterion catalysis",

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",

author = "Boying Guo and Gregg Schwarzwalder and Njardarson, {Jon T.}",

year = "2012",

month = jun,

day = "4",

doi = "10.1002/anie.201201367",

language = "English (US)",

volume = "51",

pages = "5675--5678",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "23",

}

TY - JOUR

T1 - Catalytic ring expansion of vinyl oxetanes

T2 - Asymmetric synthesis of dihydropyrans using chiral counterion catalysis

AU - Guo, Boying

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

UR - http://www.scopus.com/inward/record.url?scp=84861637785&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84861637785&partnerID=8YFLogxK

U2 - 10.1002/anie.201201367

DO - 10.1002/anie.201201367

M3 - Article

C2 - 22528273

AN - SCOPUS:84861637785

SN - 1433-7851

VL - 51

SP - 5675

EP - 5678

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 23

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this