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Stepwise fabrication and architecture of heterogeneous 9-thiourea epiquinine catalyst with excellent enantioselectivity in the asymmetric Friedel–Crafts reaction of indoles with imines

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Abstract.
Heterogeneous 9-thiourea epiquinine catalysts are prepared by covalently anchoring 9-(3,5-is(trifluoromethyl)
phenylthiourea)epiquinine on mesoporous silica surfaces via mercapto linker. It is found that 9-thiourea epiquinine moieties are located comparably on the interior and exterior surfaces of SBA-15 while preferentially on the exterior surface of MCM-41. The heterogeneous 9-thiourea epiquinine are applied as catalysts in the asymmetric Friedel–Crafts reaction of indoles with imines. SBA-15 supported 9-thiourea epiquinine, with more catalytic sites inside the channels, is found more chemselective and enantioselective than the counterpart supported on MCM-41. The effects of solvents and molecule dimensions of both substrates on the reaction effectiveness and selectivity are also discussed.

Keywords:
heterogeneous catalysis
Asymmetric C–C formation
9-Thiourea epiquinine
Enantioselectivity
Friedel–Crafts reaction
Mesoporous silica

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Informasi Detail

Judul Seri

Journal of Catalysis

No. Panggil

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Penerbit

London : Elsevier Inc.., 2008

Deskripsi Fisik

Journal of Catalysis 260 (2008) 81–85

Bahasa

English

ISBN/ISSN

00219517

Klasifikasi

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Tipe Isi

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Tipe Media

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Tipe Pembawa

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Edisi

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Subjek

KIMIA

Info Detail Spesifik

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Pernyataan Tanggungjawab

agus

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