Kinetic Evidence for Dihapto (η2) π-Aryl Participation in Acid-Catalyzed Ring Opening of Diarylhomobenzoquinone Epoxides

Haruyasu Asahara; Kohta Saito; Naohiko Ikuma; Takumi Oshima

doi:10.1021/jo902179x

Kinetic Evidence for Dihapto (η2) π-Aryl Participation in Acid-Catalyzed Ring Opening of Diarylhomobenzoquinone Epoxides

The Journal of Organic Chemistry ◽

10.1021/jo902179x ◽

2010 ◽

Vol 75 (3) ◽

pp. 733-740 ◽

Cited By ~ 5

Author(s):

Haruyasu Asahara ◽

Kohta Saito ◽

Naohiko Ikuma ◽

Takumi Oshima

Keyword(s):

Ring Opening ◽

Acid Catalyzed ◽

Aryl Participation

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Mechanistic evidence for remote π-aryl participation in acid-catalyzed ring opening of homobenzoquinone epoxides

Chemical Communications ◽

10.1039/b719663f ◽

2008 ◽

pp. 1804 ◽

Cited By ~ 3

Author(s):

Takumi Oshima ◽

Haruyasu Asahara ◽

Takuya Koizumi ◽

Saki Miyamoto

Keyword(s):

Ring Opening ◽

Acid Catalyzed ◽

Aryl Participation

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Synthesis of Medium-Sized Carbocycles via a Bidentate Lewis Acid-Catalyzed Inverse Electron-Demand Diels–Alder Reaction Followed by Photoinduced Ring-Opening

Organic Letters ◽

10.1021/acs.orglett.1c00249 ◽

2021 ◽

Author(s):

Julia Ruhl ◽

Sebastian Ahles ◽

Marcel A. Strauss ◽

Christopher M. Leonhardt ◽

Hermann A. Wegner

Keyword(s):

Lewis Acid ◽

Ring Opening ◽

Alder Reaction ◽

Diels Alder ◽

Inverse Electron Demand ◽

Diels Alder Reaction ◽

Acid Catalyzed ◽

Electron Demand

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Acid-Catalyzed Ring-Opening Cyclization of Spirocyclopropanes for the Construction of a 2-Arylbenzofuran Skeleton: Total Synthesis of Cuspidan B

Synthesis ◽

10.1055/s-0035-1561590 ◽

2016 ◽

Vol 48 (12) ◽

pp. 1892-1901 ◽

Cited By ~ 12

Author(s):

Hisanori Nambu ◽

Takayuki Yakura ◽

Naoki Ono

Keyword(s):

Total Synthesis ◽

Ring Opening ◽

Acid Catalyzed

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A nuclear magnetic resonance kinetic study of the acid-catalyzed epoxide ring opening of tetramethylethylene oxide

Journal of the American Chemical Society ◽

10.1021/ja00478a027 ◽

1978 ◽

Vol 100 (10) ◽

pp. 3122-3127 ◽

Cited By ~ 16

Author(s):

Y. Pocker ◽

B. P. Ronald

Keyword(s):

Nuclear Magnetic Resonance ◽

Magnetic Resonance ◽

Kinetic Study ◽

Ring Opening ◽

Epoxide Ring ◽

Epoxide Ring Opening ◽

Acid Catalyzed ◽

Nuclear Magnetic

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Transition Metal-based Lewis Acid Catalyzed Ring Opening of Epoxides Using Amines Under Solvent-Free Conditions

Synlett ◽

10.1055/s-2004-822910 ◽

2004 ◽

pp. 1122-1122

Author(s):

Li-Wen Xu ◽

Chun-Gu Xia ◽

Pei-Qing Zhao

Keyword(s):

Transition Metal ◽

Lewis Acid ◽

Ring Opening ◽

Solvent Free ◽

Solvent Free Conditions ◽

Ring Opening Of Epoxides ◽

Acid Catalyzed

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The Configuration of Atrolactic Acid. Retention of Configuration in the Acid-catalyzed Ring Opening of Stilbene Oxides1

Journal of the American Chemical Society ◽

10.1021/ja01597a054 ◽

1956 ◽

Vol 78 (16) ◽

pp. 4061-4064 ◽

Cited By ~ 49

Author(s):

James H. Brewster

Keyword(s):

Ring Opening ◽

Acid Catalyzed

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The Polyphosphoric Acid-Catalyzed Ring Opening of 4, 5-Epoxy-3-oxo Steroids. IV. The Synthesis of 17α-Hydroxy-4-ethylthiopregn-4-ene-3, 20-dione and Its Analogs

Chemical and Pharmaceutical Bulletin ◽

10.1248/cpb.15.887 ◽

1967 ◽

Vol 15 (6) ◽

pp. 887-892 ◽

Cited By ~ 2

Author(s):

Munemitsu Tomoeda ◽

Akihiko Ishida ◽

Toshitaka Koga

Keyword(s):

Ring Opening ◽

Polyphosphoric Acid ◽

Acid Catalyzed

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A Mild Procedure for the Lewis Acid-Catalyzed Ring-Opening of Activated Cyclopropanes with Amine Nucleophiles

Organic Letters ◽

10.1021/ol8009286 ◽

2008 ◽

Vol 10 (13) ◽

pp. 2809-2812 ◽

Cited By ~ 121

Author(s):

Olga Lifchits ◽

André B. Charette

Keyword(s):

Lewis Acid ◽

Ring Opening ◽

Acid Catalyzed

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ChemInform Abstract: Lewis Acid Catalyzed Ring-Opening Reactions of Semicyclic N,O-Acetals Possessing an Exocyclic Nitrogen Atom: Mechanistic Aspect and Application to Piperidine Alkaloid Synthesis.

ChemInform ◽

10.1002/chin.200221061 ◽

2010 ◽

Vol 33 (21) ◽

pp. no-no

Author(s):

Masaharu Sugiura ◽

Hiroyuki Hagio ◽

Ryoji Hirabayashi ◽

Shu Kobayashi

Keyword(s):

Nitrogen Atom ◽

Lewis Acid ◽

Ring Opening ◽

Alkaloid Synthesis ◽

Ring Opening Reactions ◽

Acid Catalyzed ◽

Mechanistic Aspect ◽

Exocyclic Nitrogen Atom

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Synthesis of medium-sized cyclic γ-haloketones by radical mediated ring-opening reaction of Lewis acid catalyzed (2+2)-cycloaddition products

Tetrahedron Letters ◽

10.1016/j.tetlet.2004.12.024 ◽

2005 ◽

Vol 46 (6) ◽

pp. 1005-1008 ◽

Cited By ~ 18

Author(s):

Kiyosei Takasu ◽

Satoshi Nagao ◽

Masataka Ihara

Keyword(s):

Lewis Acid ◽

Ring Opening ◽

Ring Opening Reaction ◽

Acid Catalyzed

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