Stereoselective Synthesis of .beta.-Oxygenated .alpha.-Hydroxyphosphonates by Lewis Acid-Mediated Stereoselective Hydrophosphonylation of .alpha.-Benzyloxy Aldehydes. An Application to the Synthesis of Phosphonic Acid Analogs of Oxyamino Acids

Tsutomu Yokomatsu; Yoshinori Yoshida; Shiroshi Shibuya

doi:10.1021/jo00104a064

Stereoselective Synthesis of .beta.-Oxygenated .alpha.-Hydroxyphosphonates by Lewis Acid-Mediated Stereoselective Hydrophosphonylation of .alpha.-Benzyloxy Aldehydes. An Application to the Synthesis of Phosphonic Acid Analogs of Oxyamino Acids

The Journal of Organic Chemistry ◽

10.1021/jo00104a064 ◽

1994 ◽

Vol 59 (25) ◽

pp. 7930-7933 ◽

Cited By ~ 97

Author(s):

Tsutomu Yokomatsu ◽

Yoshinori Yoshida ◽

Shiroshi Shibuya

Keyword(s):

Lewis Acid ◽

Phosphonic Acid ◽

Stereoselective Synthesis

Download Full-text

ChemInform Abstract: Stereoselective Synthesis of β-Oxygenated α- Hydroxyphosphonates by Lewis Acid-Mediated Stereoselective Hydrophosphonylation of α-Benzyloxy Aldehydes. An Application to the Synthesis of Phosphonic Acid Analogues of Oxyamino Acids.

ChemInform ◽

10.1002/chin.199526191 ◽

2010 ◽

Vol 26 (26) ◽

pp. no-no

Author(s):

T. YOKOMATSU ◽

Y. YOSHIDA ◽

S. SHIBUYA

Keyword(s):

Lewis Acid ◽

Phosphonic Acid ◽

Stereoselective Synthesis

Download Full-text

Catalytic Stereoselective Synthesis of α-Amino Phosphonic Acid Derivatives by Asymmetric Hydrogenation

Synthetic Communications ◽

10.1080/00397919608003678 ◽

1996 ◽

Vol 24 (4) ◽

pp. 777-781 ◽

Cited By ~ 4

Author(s):

Ute Schmidt ◽

Günther Oehme ◽

Hanswalter Krause

Keyword(s):

Phosphonic Acid ◽

Stereoselective Synthesis ◽

Asymmetric Hydrogenation

Download Full-text

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

Download Full-text

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

Download Full-text

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

Download Full-text

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

Download Full-text

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.

Download Full-text

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

Download Full-text

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.

Download Full-text

An N-Heterocyclic Carbene/Lewis Acid Strategy for the Stereoselective Synthesis of Spirooxindole Lactones

Angewandte Chemie ◽

10.1002/ange.201201643 ◽

2012 ◽

Vol 124 (20) ◽

pp. 5047-5051 ◽

Cited By ~ 87

Author(s):

Julien Dugal-Tessier ◽

Elizabeth A. O'Bryan ◽

Thomas B. H. Schroeder ◽

Daniel T. Cohen ◽

Karl A. Scheidt

Keyword(s):

Lewis Acid ◽

Stereoselective Synthesis

Download Full-text

Stereoselective Synthesis of .beta.-Oxygenated .alpha.-Hydroxyphosphonates by Lewis Acid-Mediated Stereoselective Hydrophosphonylation of .alpha.-Benzyloxy Aldehydes. An Application to the Synthesis of Phosphonic Acid Analogs of Oxyamino Acids

ChemInform Abstract: Stereoselective Synthesis of β-Oxygenated α- Hydroxyphosphonates by Lewis Acid-Mediated Stereoselective Hydrophosphonylation of α-Benzyloxy Aldehydes. An Application to the Synthesis of Phosphonic Acid Analogues of Oxyamino Acids.

Catalytic Stereoselective Synthesis of α-Amino Phosphonic Acid Derivatives by Asymmetric Hydrogenation

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.

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

An N-Heterocyclic Carbene/Lewis Acid Strategy for the Stereoselective Synthesis of Spirooxindole Lactones

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