Acid-catalyzed chirality-transferring intramolecular Friedel–Crafts cyclization of α-hydroxy-α-alkenylsilanes

Kazuhiko Sakaguchi; Shunnichi Kubota; Wataru Akagi; Naoko Ikeda; Masato Higashino; Shoma Ariyoshi; Tetsuro Shinada; Yasufumi Ohfune; Takahiro Nishimura

doi:10.1039/c9cc03509e

Acid-catalyzed chirality-transferring intramolecular Friedel–Crafts cyclization of α-hydroxy-α-alkenylsilanes

Chemical Communications ◽

10.1039/c9cc03509e ◽

2019 ◽

Vol 55 (59) ◽

pp. 8635-8638 ◽

Cited By ~ 1

Author(s):

Kazuhiko Sakaguchi ◽

Shunnichi Kubota ◽

Wataru Akagi ◽

Naoko Ikeda ◽

Masato Higashino ◽

...

Keyword(s):

Benzene Ring ◽

Lewis Acid ◽

Optically Active ◽

Acid Catalyzed

Acid-catalyzed intramolecular Friedel–Crafts cyclization of optically active α-hydroxy-α-alkenylsilanes possessing a benzene ring (>99% ee) with TMSOTf as a Lewis acid gave enantio-enriched tetrahydronaphthalenes (up to 98% ee).

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ChemInform Abstract: The Preparation of Optically Active δ2-Isoxazolines. A Model for Asymmetric Induction in the Non Lewis Acid Catalyzed Reactions of Oppolzer′s Chiral Sultam.

ChemInform ◽

10.1002/chin.198852160 ◽

1988 ◽

Vol 19 (52) ◽

Author(s):

D. P. CURRAN ◽

B. H. KIM ◽

J. DAUGHERTY ◽

T. A. HEFFNER

Keyword(s):

Lewis Acid ◽

Optically Active ◽

Asymmetric Induction ◽

Acid Catalyzed ◽

Catalyzed Reactions

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Inside Cover: Lewis-Acid-Catalyzed Intramolecular Aza-Friedel-Crafts Reaction ofN-tert-Butanesulfinyl Imines: Efficient Synthesis of Optically Active 9-Aminofluorene Derivatives (Asian J. Org. Chem. 1/2013)

Asian Journal of Organic Chemistry ◽

10.1002/ajoc.201390001 ◽

2013 ◽

Vol 2 (1) ◽

pp. 2-2 ◽

Cited By ~ 1

Author(s):

Yi Li ◽

Ming-Hua Xu

Keyword(s):

Lewis Acid ◽

Optically Active ◽

Efficient Synthesis ◽

Acid Catalyzed

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Lewis-Acid-Catalyzed Intramolecular Aza-Friedel-Crafts Reaction ofN-tert-Butanesulfinyl Imines: Efficient Synthesis of Optically Active 9-Aminofluorene Derivatives

Asian Journal of Organic Chemistry ◽

10.1002/ajoc.201200161 ◽

2013 ◽

Vol 2 (1) ◽

pp. 50-53 ◽

Cited By ~ 8

Author(s):

Yi Li ◽

Ming-Hua Xu

Keyword(s):

Lewis Acid ◽

Optically Active ◽

Efficient Synthesis ◽

Acid Catalyzed

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Transition-metal mediated exo selective and enantioselective Diels–Alder reactions for the preparation of octalones with unusual stereochemistries. Reactions of 2-cobaloxime substituted 1,3-dienes with cyclohexenone in optically active Lewis acid catalyzed [4+2] cycloadditions

Journal of Organometallic Chemistry ◽

10.1016/s0022-328x(98)01036-5 ◽

1999 ◽

Vol 577 (1) ◽

pp. 120-125 ◽

Cited By ~ 6

Author(s):

B.Matthew Richardson ◽

Cynthia S Day ◽

Mark E Welker

Keyword(s):

Transition Metal ◽

Lewis Acid ◽

Optically Active ◽

Diels Alder ◽

Acid Catalyzed

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ChemInform Abstract: A Highly Asymmetric, Lewis Acid-Catalyzed Diels-Alder Reaction Using Optically Active 2-(3-Tolyl-p-sulfinyl)furyl α,β- Unsaturated Ketones as a Dienophile.

ChemInform ◽

10.1002/chin.199634107 ◽

2010 ◽

Vol 27 (34) ◽

pp. no-no

Author(s):

Y. ARAI ◽

T. MASUDA ◽

Y. MASAKI ◽

M. SHIRO

Keyword(s):

Lewis Acid ◽

Alder Reaction ◽

Optically Active ◽

Diels Alder ◽

Unsaturated Ketones ◽

Diels Alder Reaction ◽

Acid Catalyzed

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ChemInform Abstract: Enantioselective Aldol Chemistry via Alkyl Enol Ethers. Scope of the Lewis Acid Catalyzed Condensation of Optically Active Trimethylsilyl and Methyl 2-((E)-1-Alkenyloxy)ethanoates with Acetals.

ChemInform ◽

10.1002/chin.199135048 ◽

2010 ◽

Vol 22 (35) ◽

pp. no-no

Author(s):

J. A. FAUNCE ◽

B. A. GRISSO ◽

P. B. MACKENZIE

Keyword(s):

Lewis Acid ◽

Optically Active ◽

Enol Ethers ◽

Acid Catalyzed ◽

Alkyl Enol Ethers

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ChemInform Abstract: The Lewis Acid-Catalyzed Intramolecular Asymmetric Hetero-Diels-Alder Reaction of Chiral α′-Sulfinyl α,β-Unsaturated Ketone. A Chiral Diene Bearing an Optically Active Sulfinylmethyl Group.

ChemInform ◽

10.1002/chin.199329151 ◽

2010 ◽

Vol 24 (29) ◽

pp. no-no

Author(s):

K. HIROI ◽

M. UMEMURA ◽

Y. TOMIKAWA

Keyword(s):

Lewis Acid ◽

Alder Reaction ◽

Optically Active ◽

Diels Alder ◽

Unsaturated Ketone ◽

Diels Alder Reaction ◽

Acid Catalyzed

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ChemInform Abstract: LEWIS ACID CATALYZED ACYL MIGRATION WITH OPTICALLY ACTIVE (Z)- AND (E)-1,3-DIPHENYL-2-BUTEN-1-ONE OXIDE. EVIDENCE OF A CONCERTED PATHWAY

Chemischer Informationsdienst ◽

10.1002/chin.197825113 ◽

1978 ◽

Vol 9 (25) ◽

Author(s):

J. M. DOMAGALA ◽

R. D. BACH

Keyword(s):

Lewis Acid ◽

Acyl Migration ◽

Optically Active ◽

Acid Catalyzed

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The Lewis Acid-catalyzed Intramolecular Asymmetric Hetero Diels-Alder Reaction of Chiral a'-Sulfinyl-a,b-unsaturated Ketone. A Chiral Diene Bearing an Optically Active Sulfinylmethyl Group

Heterocycles ◽

10.3987/com-92-s27 ◽

1993 ◽

Vol 35 (1) ◽

pp. 73 ◽

Cited By ~ 7

Author(s):

Kunio Hiroi ◽

Masayuki Umemura ◽

Yoko Tomikawa

Keyword(s):

Lewis Acid ◽

Alder Reaction ◽

Optically Active ◽

Diels Alder ◽

Unsaturated Ketone ◽

Diels Alder Reaction ◽

Acid Catalyzed

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Stereochemistry in Lewis acid-catalyzed silylation of alcohols, silanols, and methoxysilanes with optically active methyl(1-naphthyl)phenylsilane

Silicon Chemistry ◽

10.1007/s11201-007-9026-y ◽

2007 ◽

Vol 3 (5) ◽

pp. 243-249 ◽

Cited By ~ 32

Author(s):

Satoshi Shinke ◽

Teruhisa Tsuchimoto ◽

Yusuke Kawakami

Keyword(s):

Lewis Acid ◽

Optically Active ◽

Active Methyl ◽

Acid Catalyzed

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