Enantioselective Synthesis of Planar-Chiral 1, n -Dioxa[ n ]paracyclophane-Based Phosphites and Their Application as Chiral Ligands

Takanori Shibata, Miku Fukai, Ryosuke Sekine, Madhurima Hazra, Stephen Kyalo Kanyiva

Research output: Contribution to journalReview article

4 Citations (Scopus)

Abstract

Various planar-chiral 1,n-dioxa[n]paracyclophanes possessing a phenolic hydroxyl group have been synthesized via enantioselective ortho-lithiation. Subsequent reaction with 2,2′-biarylene phosphorochloridites gave a new family of chiral phosphites. These phosphites were then used as chiral ligands in the enantioselective palladium-catalyzed allylic alkylation of dimethyl malonate with (E)-1,3-diphenylallyl acetate and the rhodium-catalyzed 1,4-addition of phenylboronic acid to cyclohex-2-enone.

Original languageEnglish
Article numberss-2016-c0168-st
Pages (from-to)2664-2670
Number of pages7
JournalSynthesis (Germany)
Volume48
Issue number16
DOIs
Publication statusPublished - 2016 Aug 16

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Phosphites
Alkylation
Rhodium
Palladium
Ligands
Acids
Hydroxyl Radical
Acetates
benzeneboronic acid
methyl malonate

Keywords

  • 1,4-addition
  • allylic alkylation
  • chiral ligands
  • paracyclophanes
  • phosphites
  • planar chirality

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Enantioselective Synthesis of Planar-Chiral 1, n -Dioxa[ n ]paracyclophane-Based Phosphites and Their Application as Chiral Ligands. / Shibata, Takanori; Fukai, Miku; Sekine, Ryosuke; Hazra, Madhurima; Kanyiva, Stephen Kyalo.

In: Synthesis (Germany), Vol. 48, No. 16, ss-2016-c0168-st, 16.08.2016, p. 2664-2670.

Research output: Contribution to journalReview article

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AU - Hazra, Madhurima

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