Regio- and Stereoselective Synthesis ofNor-Nonactinic Acid Derivatives—Kinetic Reaction Control in the Lewis Acid Mediated Domino Reaction of 1,3-Dicarbonyl Dianions with 1-Bromo-2,3-epoxypropanes

A Lewis acid catalyzed cationic domino reaction involving sequential electrocyclization and polar addition of allenol ethers onto the resulting oxyallyl species is described. The overall sequence allows a highly stereoselective synthesis of densely substituted cyclopentanoid compounds containing α-formylvinyl functionality which is formally equivalent to products of a Morita–Baylis–Hillman alkylation process.

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Catalyst- and Substituent-Controlled Regio- and Stereoselective Synthesis of Indolyl Acrylates by Lewis-Acid-Catalyzed Direct Functionalization of 3-Formylindoles with Diazo Esters

Organic Letters ◽

10.1021/acs.orglett.1c00277 ◽

2021 ◽

Vol 23 (6) ◽

pp. 2140-2146

Author(s):

Sana Jamshaid ◽

Shreedhar Devkota ◽

Yong Rok Lee

Keyword(s):

Lewis Acid ◽

Stereoselective Synthesis ◽

Diazo Esters ◽

Direct Functionalization ◽

Acid Catalyzed

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ChemInform Abstract: Lewis Acid Promoted Hetero [2 + 2] Cycloaddition Reactions of Aldehydes with 10-Propynyl-9(10H)-acridone. A Highly Stereoselective Synthesis of Acrylic Acid Derivatives and 1,3-Dienes Using an Electron Deficient Variant of Ynamine.

ChemInform ◽

10.1002/chin.200003085 ◽

2010 ◽

Vol 31 (3) ◽

pp. no-no

Author(s):

Richard P. Hsung ◽

Craig A. Zificsak ◽

Lin-Li Wei ◽

Christopher J. Douglas ◽

Hui Xiong ◽

...

Keyword(s):

Acrylic Acid ◽

Lewis Acid ◽

Stereoselective Synthesis ◽

Cycloaddition Reactions

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Stereoselective Synthesis of C-Ketosides by Lewis Acid Catalyzed C-Glycosylation of Alkynyl-Ketoses.

ChemInform ◽

10.1002/chin.200314203 ◽

2003 ◽

Vol 34 (14) ◽

Author(s):

Ana M. Gomez ◽

Clara Uriel ◽

Serafin Valverde ◽

Slawomir Jarosz ◽

J. Cristobal Lopez

Keyword(s):

Lewis Acid ◽

Stereoselective Synthesis ◽

Acid Catalyzed

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ChemInform Abstract: Domino-Reaction of Oxal(imidoyl)chlorides with 3-Aminoisoxazoles: Regio- and Stereoselective Synthesis of 1,4-Dihydro-imidazo[4,5-b]quinoxalines.

ChemInform ◽

10.1002/chin.199931047 ◽

2010 ◽

Vol 30 (31) ◽

pp. no-no

Author(s):

Joerg Wuckelt ◽

Manfred Doering ◽

Peter Langer ◽

Rainer Beckert

Keyword(s):

Stereoselective Synthesis ◽

Domino Reaction ◽

Imidoyl Chlorides

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Pd-Catalyzed Three-Component Domino Reaction of Vinyl Benzoxazinanones for Regioselective and Stereoselective Synthesis of Allylic Sulfone-Containing Amino Acid Derivatives

Organic Letters ◽

10.1021/acs.orglett.8b03440 ◽

2018 ◽

Vol 20 (24) ◽

pp. 7888-7892 ◽

Cited By ~ 12

Author(s):

Jiping Hao ◽

Yi Xu ◽

Zhongliang Xu ◽

Zhiqiang Zhang ◽

Weibo Yang

Keyword(s):

Amino Acid ◽

Stereoselective Synthesis ◽

Domino Reaction ◽

Amino Acid Derivatives

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Stereoselective Synthesis of CF3-Substituted Aziridines by Lewis Acid Mediated Aziridination of Aldimines with Diazoacetates.

ChemInform ◽

10.1002/chin.200333112 ◽

2003 ◽

Vol 34 (33) ◽

Author(s):

Takahiko Akiyama ◽

Satoshi Ogi ◽

Kohei Fuchibe

Keyword(s):

Lewis Acid ◽

Stereoselective Synthesis

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Counterion effects in the catalytic stereoselective synthesis of 2,3′-pyrrolidinyl spirooxindoles

Chemical Communications ◽

10.1039/c3cc47767c ◽

2014 ◽

Vol 50 (40) ◽

pp. 5242-5244 ◽

Cited By ~ 20

Author(s):

Jacob P. MacDonald ◽

Benjamin H. Shupe ◽

John D. Schreiber ◽

Annaliese K. Franz

Keyword(s):

Lewis Acid ◽

Stereoselective Synthesis ◽

Acid Catalyzed

A Lewis acid-catalyzed stereoselective [3+2] annulation of crotylsilanes with iminooxindoles is reported to access 2,3′-pyrrolidinyl spirooxindoles with four stereocenters.

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ChemInform Abstract: Lewis Acid Promoted [2 + 1] Cycloaddition Reactions of a 1-Seleno-2-silylethene to 2-Phosphonoacrylates: Stereoselective Synthesis of a Novel Functionalized α-Aminocyclopropanephosphonic Acid.

ChemInform ◽

10.1002/chin.199903074 ◽

2010 ◽

Vol 30 (3) ◽

pp. no-no

Author(s):

S. YAMAZAKI ◽

T. TAKADA ◽

T. IMANISHI ◽

Y. MORIGUCHI ◽

S. YAMABE

Keyword(s):

Lewis Acid ◽

Stereoselective Synthesis ◽

Cycloaddition Reactions

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Regio- and Stereoselective Synthesis ofNor-Nonactinic Acid Derivatives—Kinetic Reaction Control in the Lewis Acid Mediated Domino Reaction of 1,3-Dicarbonyl Dianions with 1-Bromo-2,3-epoxypropanes

ChemInform Abstract: Regio- and Stereoselective Synthesis of Nor-Nonactinic Acid Derivatives - Kinetic Reaction Control in the Lewis Acid Mediated Domino Reaction of 1,3-Dicarbonyl Dianions with 1-Bromo-2,3-epoxypropanes.

Intercepting the Nazarov Oxyallyl Intermediate with α-Formyl­vinyl Anion Equivalents to Access Formal Morita–Baylis–Hillman Alkylation Products

Catalyst- and Substituent-Controlled Regio- and Stereoselective Synthesis of Indolyl Acrylates by Lewis-Acid-Catalyzed Direct Functionalization of 3-Formylindoles with Diazo Esters

ChemInform Abstract: Lewis Acid Promoted Hetero [2 + 2] Cycloaddition Reactions of Aldehydes with 10-Propynyl-9(10H)-acridone. A Highly Stereoselective Synthesis of Acrylic Acid Derivatives and 1,3-Dienes Using an Electron Deficient Variant of Ynamine.

Stereoselective Synthesis of C-Ketosides by Lewis Acid Catalyzed C-Glycosylation of Alkynyl-Ketoses.

ChemInform Abstract: Domino-Reaction of Oxal(imidoyl)chlorides with 3-Aminoisoxazoles: Regio- and Stereoselective Synthesis of 1,4-Dihydro-imidazo[4,5-b]quinoxalines.

Pd-Catalyzed Three-Component Domino Reaction of Vinyl Benzoxazinanones for Regioselective and Stereoselective Synthesis of Allylic Sulfone-Containing Amino Acid Derivatives

Stereoselective Synthesis of CF3-Substituted Aziridines by Lewis Acid Mediated Aziridination of Aldimines with Diazoacetates.

Counterion effects in the catalytic stereoselective synthesis of 2,3′-pyrrolidinyl spirooxindoles

ChemInform Abstract: Lewis Acid Promoted [2 + 1] Cycloaddition Reactions of a 1-Seleno-2-silylethene to 2-Phosphonoacrylates: Stereoselective Synthesis of a Novel Functionalized α-Aminocyclopropanephosphonic Acid.

Intercepting the Nazarov Oxyallyl Intermediate with α-Formylvinyl Anion Equivalents to Access Formal Morita–Baylis–Hillman Alkylation Products