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

doi:10.1055/s-0035-1562097

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

Global Center for Science and Engineering

Research output: Contribution to journal › Review 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 language	English
Article number	ss-2016-c0168-st
Pages (from-to)	2664-2670
Number of pages	7
Journal	Synthesis (Germany)
Volume	48
Issue number	16
DOIs	https://doi.org/10.1055/s-0035-1562097
Publication status	Published - 2016 Aug 16

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Keywords

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

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Cite this

Shibata, T., Fukai, M., Sekine, R., Hazra, M., & Kanyiva, S. K. (2016). Enantioselective Synthesis of Planar-Chiral 1, n -Dioxa[ n ]paracyclophane-Based Phosphites and Their Application as Chiral Ligands. Synthesis (Germany), 48(16), 2664-2670. [ss-2016-c0168-st]. https://doi.org/10.1055/s-0035-1562097

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 journal › Review article

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10.1055/s-0035-1562097