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; Kyalo Stephen 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, Kyalo Stephen Kanyiva

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Review article › peer-review

5 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

Keywords

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

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-0035-1562097

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

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.",

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

author = "Takanori Shibata and Miku Fukai and Ryosuke Sekine and Madhurima Hazra and Kanyiva, {Kyalo Stephen}",

note = "Funding Information: This work was supported by JST, ACT-C. We are grateful to Tokyo Chemical Industry Co., Ltd. (TCI) for generous support with 1,11-dioxa[11]paracyclophane supply. M.F. and R.S. contributed equally to this work Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart, New York.",

year = "2016",

month = aug,

day = "16",

doi = "10.1055/s-0035-1562097",

language = "English",

volume = "48",

pages = "2664--2670",

journal = "Synthesis (Germany)",

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publisher = "Georg Thieme Verlag",

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TY - JOUR

T1 - Enantioselective Synthesis of Planar-Chiral 1, n -Dioxa[ n ]paracyclophane-Based Phosphites and Their Application as Chiral Ligands

AU - Shibata, Takanori

AU - Fukai, Miku

AU - Sekine, Ryosuke

AU - Hazra, Madhurima

AU - Kanyiva, Kyalo Stephen

N1 - Funding Information: This work was supported by JST, ACT-C. We are grateful to Tokyo Chemical Industry Co., Ltd. (TCI) for generous support with 1,11-dioxa[11]paracyclophane supply. M.F. and R.S. contributed equally to this work Publisher Copyright: © Georg Thieme Verlag Stuttgart, New York.

PY - 2016/8/16

Y1 - 2016/8/16

N2 - 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.

AB - 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.

KW - 1,4-addition

KW - allylic alkylation

KW - chiral ligands

KW - paracyclophanes

KW - phosphites

KW - planar chirality

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U2 - 10.1055/s-0035-1562097

DO - 10.1055/s-0035-1562097

M3 - Review article

AN - SCOPUS:84978964186

VL - 48

SP - 2664

EP - 2670

JO - Synthesis (Germany)

JF - Synthesis (Germany)

SN - 0039-7881

IS - 16

M1 - ss-2016-c0168-st

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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