Chiral copper(II) phosphate catalyzed enantioselective synthesis of isochromene derivatives by sequential intramolecular cyclization and asymmetric transfer hydrogenation of o-alkynylacetophenones

Kodai Saito, Yuki Kajiwara, Takahiko Akiyama

Research output: Contribution to journalArticle

56 Citations (Scopus)

Abstract

A good mix: The title reaction of o-alkynylacetophenones with the Hantzsch ester in the presence of a chiral copper/phosphate catalyst proceeds in good yields with excellent enantioselectivities. The key intermediate for enantiocontrol is the ion pair of the carbonyl ylide with a chiral phosphate anion, and this process provides straight forward access to highly enantioriched chiral isochromenes.

Original languageEnglish
Pages (from-to)13284-13288
Number of pages5
JournalAngewandte Chemie - International Edition
Volume52
Issue number50
DOIs
Publication statusPublished - 2013 Dec 9
Externally publishedYes

Fingerprint

Cyclization
Hydrogenation
Copper
Phosphates
Derivatives
Enantioselectivity
Anions
Esters
Negative ions
Ions
Catalysts

Keywords

  • asymmetric catalysis
  • copper
  • heterocycles
  • hydrogenation
  • ylides

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

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abstract = "A good mix: The title reaction of o-alkynylacetophenones with the Hantzsch ester in the presence of a chiral copper/phosphate catalyst proceeds in good yields with excellent enantioselectivities. The key intermediate for enantiocontrol is the ion pair of the carbonyl ylide with a chiral phosphate anion, and this process provides straight forward access to highly enantioriched chiral isochromenes.",
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T1 - Chiral copper(II) phosphate catalyzed enantioselective synthesis of isochromene derivatives by sequential intramolecular cyclization and asymmetric transfer hydrogenation of o-alkynylacetophenones

AU - Saito, Kodai

AU - Kajiwara, Yuki

AU - Akiyama, Takahiko

PY - 2013/12/9

Y1 - 2013/12/9

N2 - A good mix: The title reaction of o-alkynylacetophenones with the Hantzsch ester in the presence of a chiral copper/phosphate catalyst proceeds in good yields with excellent enantioselectivities. The key intermediate for enantiocontrol is the ion pair of the carbonyl ylide with a chiral phosphate anion, and this process provides straight forward access to highly enantioriched chiral isochromenes.

AB - A good mix: The title reaction of o-alkynylacetophenones with the Hantzsch ester in the presence of a chiral copper/phosphate catalyst proceeds in good yields with excellent enantioselectivities. The key intermediate for enantiocontrol is the ion pair of the carbonyl ylide with a chiral phosphate anion, and this process provides straight forward access to highly enantioriched chiral isochromenes.

KW - asymmetric catalysis

KW - copper

KW - heterocycles

KW - hydrogenation

KW - ylides

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