Electron-withdrawing, bipheny 1-2,2 -diol-based compounds for asymmetric catalysis

Elisa G. Gutierrez; Eric J. Moorhead; Eva H. Smith; Vivian Lin; Laura K.G. Ackerman; Claire E. Knezevic; Victoria Sun; Sharday Grant; Anna G. Wenzel

doi:10.1002/ejoc.201000070

Electron-withdrawing, bipheny 1-2,2 -diol-based compounds for asymmetric catalysis

Elisa G. Gutierrez, Eric J. Moorhead, Eva H. Smith, Vivian Lin, Laura K.G. Ackerman, Claire E. Knezevic, Victoria Sun, Sharday Grant, Anna G. Wenzel

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

Abstract

Facile synthetic routes to a chiral chloro-substituted biphenyl-2,2′- diyl hydrogen phosphate and a chiral O,O-biphenyl-2,2′-diyl phosphoramidothioate are described. The performance of these compounds as catalysts for the hydrophosphorylation of imines and the Friedel-Crafts alkylation of indole was investigated. In the latter reaction, the chlorosubstituted phosphoric acid derivative was found to rival the best Bronsted acid catalysts reported to date.

Original language	English (US)
Pages (from-to)	3027-3031
Number of pages	5
Journal	European Journal of Organic Chemistry
Issue number	16
DOIs	https://doi.org/10.1002/ejoc.201000070
State	Published - Jun 2010
Externally published	Yes

Keywords

Asymmetric catalysis
Biaryls
Chiral resolution
Organocatalysis

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1002/ejoc.201000070

Cite this

@article{57100be367a94ee3be9b19fcd2657a84,

title = "Electron-withdrawing, bipheny 1-2,2 -diol-based compounds for asymmetric catalysis",

abstract = "Facile synthetic routes to a chiral chloro-substituted biphenyl-2,2′- diyl hydrogen phosphate and a chiral O,O-biphenyl-2,2′-diyl phosphoramidothioate are described. The performance of these compounds as catalysts for the hydrophosphorylation of imines and the Friedel-Crafts alkylation of indole was investigated. In the latter reaction, the chlorosubstituted phosphoric acid derivative was found to rival the best Bronsted acid catalysts reported to date.",

keywords = "Asymmetric catalysis, Biaryls, Chiral resolution, Organocatalysis",

author = "Gutierrez, {Elisa G.} and Moorhead, {Eric J.} and Smith, {Eva H.} and Vivian Lin and Ackerman, {Laura K.G.} and Knezevic, {Claire E.} and Victoria Sun and Sharday Grant and Wenzel, {Anna G.}",

year = "2010",

month = jun,

doi = "10.1002/ejoc.201000070",

language = "English (US)",

pages = "3027--3031",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "16",

}

TY - JOUR

T1 - Electron-withdrawing, bipheny 1-2,2 -diol-based compounds for asymmetric catalysis

AU - Gutierrez, Elisa G.

AU - Moorhead, Eric J.

AU - Smith, Eva H.

AU - Lin, Vivian

AU - Ackerman, Laura K.G.

AU - Knezevic, Claire E.

AU - Sun, Victoria

AU - Grant, Sharday

AU - Wenzel, Anna G.

PY - 2010/6

Y1 - 2010/6

N2 - Facile synthetic routes to a chiral chloro-substituted biphenyl-2,2′- diyl hydrogen phosphate and a chiral O,O-biphenyl-2,2′-diyl phosphoramidothioate are described. The performance of these compounds as catalysts for the hydrophosphorylation of imines and the Friedel-Crafts alkylation of indole was investigated. In the latter reaction, the chlorosubstituted phosphoric acid derivative was found to rival the best Bronsted acid catalysts reported to date.

AB - Facile synthetic routes to a chiral chloro-substituted biphenyl-2,2′- diyl hydrogen phosphate and a chiral O,O-biphenyl-2,2′-diyl phosphoramidothioate are described. The performance of these compounds as catalysts for the hydrophosphorylation of imines and the Friedel-Crafts alkylation of indole was investigated. In the latter reaction, the chlorosubstituted phosphoric acid derivative was found to rival the best Bronsted acid catalysts reported to date.

KW - Asymmetric catalysis

KW - Biaryls

KW - Chiral resolution

KW - Organocatalysis

UR - http://www.scopus.com/inward/record.url?scp=77952587898&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77952587898&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201000070

DO - 10.1002/ejoc.201000070

M3 - Article

AN - SCOPUS:77952587898

SN - 1434-193X

SP - 3027

EP - 3031

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 16

ER -

Electron-withdrawing, bipheny 1-2,2 -diol-based compounds for asymmetric catalysis

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this