Intramolecular Oxonium Ylide Formation–[2,3] Sigmatropic Rearrangement of Diazocarbonyl-Substituted Cyclic Unsaturated Acetals: A Formal Synthesis of Hyperolactone C

David M. Hodgson; Stanislav Man; Kimberley J. Powell; Ziga Perko; Minxiang Zeng; Elena Moreno-Clavijo; Amber L. Thompson; Michael D. Moore

doi:10.1021/jo501893r

Intramolecular Oxonium Ylide Formation–[2,3] Sigmatropic Rearrangement of Diazocarbonyl-Substituted Cyclic Unsaturated Acetals: A Formal Synthesis of Hyperolactone C

The Journal of Organic Chemistry ◽

10.1021/jo501893r ◽

2014 ◽

Vol 79 (20) ◽

pp. 9728-9734 ◽

Cited By ~ 10

Author(s):

David M. Hodgson ◽

Stanislav Man ◽

Kimberley J. Powell ◽

Ziga Perko ◽

Minxiang Zeng ◽

...

Keyword(s):

Sigmatropic Rearrangement ◽

Formal Synthesis ◽

Oxonium Ylide

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Enantioselective Construction of a 2,8-Dioxabicyclo[3.2.1]octane Ring System via [2,3]-Sigmatropic Rearrangement of Oxonium Ylide Using Chiral Dirhodium(II) Carboxylates

Chemistry Letters ◽

10.1246/cl.2009.488 ◽

2009 ◽

Vol 38 (5) ◽

pp. 488-489 ◽

Cited By ~ 34

Author(s):

Naoyuki Shimada ◽

Seiichi Nakamura ◽

Masahiro Anada ◽

Motoo Shiro ◽

Shunichi Hashimoto

Keyword(s):

Ring System ◽

Sigmatropic Rearrangement ◽

Oxonium Ylide

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Ring expansion of trans-divinyl ethylene oxide by oxonium ylide [2,3] sigmatropic rearrangement

Tetrahedron Letters ◽

10.1016/j.tetlet.2006.08.023 ◽

2006 ◽

Vol 47 (41) ◽

pp. 7281-7283 ◽

Cited By ~ 20

Author(s):

Kevin J. Quinn ◽

Neal A. Biddick ◽

Brian A. DeChristopher

Keyword(s):

Ethylene Oxide ◽

Ring Expansion ◽

Sigmatropic Rearrangement ◽

Oxonium Ylide

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Application of a Stereoselective Rhodium(II)-Catalyzed Oxonium Ylide Formation–[2,3]-Sigmatropic Rearrangement of an α-Diazo-β-keto Ester to the Synthesis of 2-epi-Cinatrin C1 Dimethyl Ester

Synlett ◽

10.1055/s-0032-1317694 ◽

2012 ◽

Vol 24 (01) ◽

pp. 65-68 ◽

Cited By ~ 11

Author(s):

Takayuki Yakura ◽

Ayaka Ozono ◽

Katsuaki Matsui ◽

Masayuki Yamashita ◽

Tomoya Fujiwara

Keyword(s):

Dimethyl Ester ◽

Sigmatropic Rearrangement ◽

Keto Ester ◽

Oxonium Ylide

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ChemInform Abstract: Enantioselective Construction of a 2,8-Dioxabicyclo[3.2.1]octane Ring System via [2,3]-Sigmatropic Rearrangement of Oxonium Ylide Using Chiral Dirhodium(II) Carboxylates.

ChemInform ◽

10.1002/chin.200942160 ◽

2009 ◽

Vol 40 (42) ◽

Author(s):

Naoyuki Shimada ◽

Seiichi Nakamura ◽

Masahiro Anada ◽

Motoo Shiro ◽

Shunichi Hashimoto

Keyword(s):

Ring System ◽

Sigmatropic Rearrangement ◽

Oxonium Ylide

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Total Synthesis of (+)-Tanikolide by a Traceless Stereoinduction Method Using Rhodium(II)-Catalyzed Oxonium Ylide Formation–[2,3]-Sigmatropic Rearrangement and NHC-Catalyzed Ring-Expansion Lactonization

Synlett ◽

10.1055/s-0035-1561341 ◽

2016 ◽

Vol 27 (07) ◽

pp. 1106-1009 ◽

Cited By ~ 8

Author(s):

Takayuki Yakura ◽

Hisanori Nambu ◽

Hikari Jinnouchi ◽

Tomoya Fujiwara

Keyword(s):

Total Synthesis ◽

Ring Expansion ◽

Sigmatropic Rearrangement ◽

Oxonium Ylide

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Formal synthesis of ent-dysiherbaine from sulfinyl dihydropyrans by sigmatropic rearrangement and tethered aminohydroxylation

Tetrahedron Letters ◽

10.1016/j.tetlet.2007.09.103 ◽

2007 ◽

Vol 48 (46) ◽

pp. 8141-8144 ◽

Cited By ~ 16

Author(s):

Roberto Fernández de la Pradilla ◽

Nadia Lwoff ◽

Alma Viso

Keyword(s):

Sigmatropic Rearrangement ◽

Formal Synthesis

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ChemInform Abstract: Total Synthesis of (+)-Tanikolide by a Traceless Stereoinduction Method Using Rhodium(II)-Catalyzed Oxonium Ylide Formation-[2,3]-Sigmatropic Rearrangement and NHC-Catalyzed Ring-Expansion Lactonization.

ChemInform ◽

10.1002/chin.201635162 ◽

2016 ◽

Vol 47 (35) ◽

Author(s):

Hisanori Nambu ◽

Hikari Jinnouchi ◽

Tomoya Fujiwara ◽

Takayuki Yakura

Keyword(s):

Total Synthesis ◽

Ring Expansion ◽

Sigmatropic Rearrangement ◽

Oxonium Ylide

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Rh(II)-binaphthol phosphate catalysts in the enantioselective intramolecular oxonium ylide formation–[3,2] sigmatropic rearrangement of α-diazo-β-ketoesters

Tetrahedron Asymmetry ◽

10.1016/s0957-4166(01)00147-1 ◽

2001 ◽

Vol 12 (6) ◽

pp. 877-881 ◽

Cited By ~ 42

Author(s):

David M. Hodgson ◽

Margarita Petroliagi

Keyword(s):

Sigmatropic Rearrangement ◽

Oxonium Ylide

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ChemInform Abstract: Rh(II)-Binaphthol Phosphate Catalysts in the Enantioselective Intramolecular Oxonium Ylide Formation-[3,2] Sigmatropic Rearrangement of α-Diazo-β-ketoesters.

ChemInform ◽

10.1002/chin.200136034 ◽

2010 ◽

Vol 32 (36) ◽

pp. no-no

Author(s):

David M. Hodgson ◽

Margarita Petroliagi

Keyword(s):

Sigmatropic Rearrangement ◽

Oxonium Ylide

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Macrocyclic oxonium ylide formation and internal [2,3]-sigmatropic rearrangement. Catalyst influence on selectivity

Tetrahedron Letters ◽

10.1016/s0040-4039(97)01160-x ◽

1997 ◽

Vol 38 (30) ◽

pp. 5265-5268 ◽

Cited By ~ 24

Author(s):

Michael P. Doyle ◽

Chad S. Peterson

Keyword(s):

Sigmatropic Rearrangement ◽

Oxonium Ylide

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