Substrate-Controlled Selective Proximal and Distal C−C Bond Cleavage via Lewis Acid Mediated O-Acylation of 2-(Arylmethylene)cyclopropylaldehyde: A Stereoselective Synthesis of Bifunctional Methylenecyclobutanes and 1,3-Conjugated Dienes

Xian Huang; Maozhong Miao

doi:10.1021/jo801021f

Substrate-Controlled Selective Proximal and Distal C−C Bond Cleavage via Lewis Acid Mediated O-Acylation of 2-(Arylmethylene)cyclopropylaldehyde: A Stereoselective Synthesis of Bifunctional Methylenecyclobutanes and 1,3-Conjugated Dienes

The Journal of Organic Chemistry ◽

10.1021/jo801021f ◽

2008 ◽

Vol 73 (17) ◽

pp. 6884-6887 ◽

Cited By ~ 21

Author(s):

Xian Huang ◽

Maozhong Miao

Keyword(s):

Lewis Acid ◽

Stereoselective Synthesis ◽

Bond Cleavage ◽

Conjugated Dienes

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ChemInform Abstract: Substrate-Controlled Selective Proximal and Distal C-C Bond Cleavage via Lewis Acid Mediated O-Acylation of 2-(Arylmethylene)cyclopropylaldehyde: A Stereoselective Synthesis of Bifunctional Methylenecyclobutanes and 1,3-Conjugated Dienes.

ChemInform ◽

10.1002/chin.200903055 ◽

2009 ◽

Vol 40 (3) ◽

Author(s):

Xian Huang ◽

Maozhong Miao

Keyword(s):

Lewis Acid ◽

Stereoselective Synthesis ◽

Bond Cleavage ◽

Conjugated Dienes

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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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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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ChemInform Abstract: Stereoselective Synthesis of Z,E Conjugated Dienes: Application to the Synthesis of Insect Sex Pheromones.

ChemInform ◽

10.1002/chin.199043295 ◽

1990 ◽

Vol 21 (43) ◽

Author(s):

O. P. VIG ◽

M. L. SHARMA ◽

J. KAPUR ◽

S. THAPAR ◽

R. GUPTA

Keyword(s):

Sex Pheromones ◽

Stereoselective Synthesis ◽

Conjugated Dienes ◽

Insect Sex Pheromones ◽

Insect Sex

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The stereoselective synthesis of functionalized conjugated dienes : preparation of (E,E)-α-hydroxy dienes and of vinylallenes.

Tetrahedron Letters ◽

10.1016/s0040-4039(00)86229-2 ◽

1983 ◽

Vol 24 (43) ◽

pp. 4691-4694 ◽

Cited By ~ 17

Author(s):

R. Bloch ◽

D. Hassan ◽

X. Mandard

Keyword(s):

Stereoselective Synthesis ◽

Conjugated Dienes

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

Synlett ◽

10.1055/s-0036-1588769 ◽

2017 ◽

Vol 28 (12) ◽

pp. 1486-1490 ◽

Cited By ~ 3

Author(s):

F. West ◽

Yen-Ku Wu ◽

Rongrong Lin

Keyword(s):

Lewis Acid ◽

Stereoselective Synthesis ◽

Domino Reaction ◽

Alkylation Process ◽

Acid Catalyzed

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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Substrate-Controlled Selective Proximal and Distal C−C Bond Cleavage via Lewis Acid Mediated O-Acylation of 2-(Arylmethylene)cyclopropylaldehyde: A Stereoselective Synthesis of Bifunctional Methylenecyclobutanes and 1,3-Conjugated Dienes

ChemInform Abstract: Substrate-Controlled Selective Proximal and Distal C-C Bond Cleavage via Lewis Acid Mediated O-Acylation of 2-(Arylmethylene)cyclopropylaldehyde: A Stereoselective Synthesis of Bifunctional Methylenecyclobutanes and 1,3-Conjugated Dienes.

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.

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.

ChemInform Abstract: Stereoselective Synthesis of Z,E Conjugated Dienes: Application to the Synthesis of Insect Sex Pheromones.

The stereoselective synthesis of functionalized conjugated dienes : preparation of (E,E)-α-hydroxy dienes and of vinylallenes.

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

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