Enantioselective Sulfoxidation Catalyzed by a Bisguanidinium Diphosphatobisperoxotungstate Ion Pair

Xinyi Ye; Adhitya Mangala Putra Moeljadi; Kek Foo Chin; Hajime Hirao; Lili Zong; Choon-Hong Tan

doi:10.1002/anie.201601574

Enantioselective Sulfoxidation Catalyzed by a Bisguanidinium Diphosphatobisperoxotungstate Ion Pair

Xinyi Ye, Adhitya Mangala Putra Moeljadi, Kek Foo Chin, Hajime Hirao, Lili Zong, Choon-Hong Tan^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

66 Citations (Scopus)

Abstract

The first enantioselective tungstate-catalyzed oxidation reaction is presented. High enantioselectivities were achieved for a variety of drug-like phenyl and heterocyclic sulfides under mild conditions with H₂O₂, a cheap and environmentally friendly oxidant. Synthetic utility was demonstrated through the preparation of (S)-Lansoprazole, a commercial proton-pump inhibitor. The active ion-pair catalyst was identified to be bisguanidinium diphosphatobisperoxotungstate using Raman spectroscopy and computational studies.

Original language	English
Pages (from-to)	7101-7105
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	25
DOIs	https://doi.org/10.1002/anie.201601574
Publication status	Published - 2016
Externally published	Yes

Research Keywords

asymmetric sulfoxidation
bisguanidinium
ion-pair catalysis
lansoprazole
Raman spectroscopy

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10.1002/anie.201601574

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title = "Enantioselective Sulfoxidation Catalyzed by a Bisguanidinium Diphosphatobisperoxotungstate Ion Pair",

abstract = "The first enantioselective tungstate-catalyzed oxidation reaction is presented. High enantioselectivities were achieved for a variety of drug-like phenyl and heterocyclic sulfides under mild conditions with H2O2, a cheap and environmentally friendly oxidant. Synthetic utility was demonstrated through the preparation of (S)-Lansoprazole, a commercial proton-pump inhibitor. The active ion-pair catalyst was identified to be bisguanidinium diphosphatobisperoxotungstate using Raman spectroscopy and computational studies.",

keywords = "asymmetric sulfoxidation, bisguanidinium, ion-pair catalysis, lansoprazole, Raman spectroscopy",

author = "Xinyi Ye and Moeljadi, {Adhitya Mangala Putra} and Chin, {Kek Foo} and Hajime Hirao and Lili Zong and Choon-Hong Tan",

year = "2016",

doi = "10.1002/anie.201601574",

language = "English",

volume = "55",

pages = "7101--7105",

journal = "Angewandte Chemie - International Edition",

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TY - JOUR

T1 - Enantioselective Sulfoxidation Catalyzed by a Bisguanidinium Diphosphatobisperoxotungstate Ion Pair

AU - Ye, Xinyi

AU - Moeljadi, Adhitya Mangala Putra

AU - Chin, Kek Foo

AU - Hirao, Hajime

AU - Zong, Lili

AU - Tan, Choon-Hong

PY - 2016

Y1 - 2016

N2 - The first enantioselective tungstate-catalyzed oxidation reaction is presented. High enantioselectivities were achieved for a variety of drug-like phenyl and heterocyclic sulfides under mild conditions with H2O2, a cheap and environmentally friendly oxidant. Synthetic utility was demonstrated through the preparation of (S)-Lansoprazole, a commercial proton-pump inhibitor. The active ion-pair catalyst was identified to be bisguanidinium diphosphatobisperoxotungstate using Raman spectroscopy and computational studies.

AB - The first enantioselective tungstate-catalyzed oxidation reaction is presented. High enantioselectivities were achieved for a variety of drug-like phenyl and heterocyclic sulfides under mild conditions with H2O2, a cheap and environmentally friendly oxidant. Synthetic utility was demonstrated through the preparation of (S)-Lansoprazole, a commercial proton-pump inhibitor. The active ion-pair catalyst was identified to be bisguanidinium diphosphatobisperoxotungstate using Raman spectroscopy and computational studies.

KW - asymmetric sulfoxidation

KW - bisguanidinium

KW - ion-pair catalysis

KW - lansoprazole

KW - Raman spectroscopy

UR - http://www.scopus.com/inward/record.url?scp=84966330230&partnerID=8YFLogxK

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-84966330230&origin=recordpage

U2 - 10.1002/anie.201601574

DO - 10.1002/anie.201601574

M3 - RGC 21 - Publication in refereed journal

SN - 1433-7851

VL - 55

SP - 7101

EP - 7105

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 25

ER -

Enantioselective Sulfoxidation Catalyzed by a Bisguanidinium Diphosphatobisperoxotungstate Ion Pair

Abstract

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