scholarly journals Evidence and isolation of tetrahedral intermediates formed upon the addition of lithium carbenoids to Weinreb amides and N-acylpyrroles

2017 ◽  
Vol 53 (68) ◽  
pp. 9498-9501 ◽  
Author(s):  
Laura Castoldi ◽  
Wolfgang Holzer ◽  
Thierry Langer ◽  
Vittorio Pace
Keyword(s):  
Weinreb Amides ◽  
Tetrahedral Intermediates

Trapping tetrahedral intermediates from Weinreb amides andN-acylpyrroles.

O-AcylTEMPOs, a Modified and Fundamental, but Unexplored Carboxylic Derivative: Recent Progress in Synthetic Applications

2019 ◽  
Vol 23 (19) ◽  
pp. 2102-2121
Author(s):  
Hiroyuki Kawafuchi ◽  
Lijian Ma ◽  
Md Imran Hossain ◽  
Tsutomu Inokuchi
Keyword(s):  
Organic Synthesis ◽  
Recent Progress ◽  
Knoevenagel Condensation ◽  
Acid Synthesis ◽  
Amino Acid Synthesis ◽  
Electrophilic Amination ◽  
Weinreb Amides ◽  
Anionic Species ◽  
Diastereoselective Addition ◽  
Carbonyl Function

O-Acylated 2,2,6,6-tetramethylpiperidine-N-oxyls (abbr. O-AcylTEMPOs) are easily available and stable carboxylic derivatives, but their utility in organic synthesis is unexplored in contrast to analogues, such as the N-methoxy-N-methylamides, known as Weinreb amides. Especially, the O–N unit of the O-acylTEMPOs dictates a fairly electronwithdrawing character for the carbonyl function. This enhances the reactivity and stability of the resulting enolate ions. Accordingly, O-acylTEMPOs allow various transformations and this review encompasses seven topics: (1) Reactivity of O-acylTEMPOs towards nucleophiles and chemoselective transformations, (2) Reactivity of anionic species derived from O-acylTEMPOs, (3) E-Selective Knoevenagel condensation of acetoacetylTEMPOs and synthesis of furans, (4) Electrocyclization of 2,4-dienones derived from acetoacetic derivatives and 2-substituted enals, (5) Diastereoselective addition of amide anion to O-(2-alkenoyl)TEMPOs and β-amino acid synthesis, (6) Thermolysis of O-acylTEMPOs, and (7) Applications for Umpolung reactions using O-benzoylTEMPOs, useful for the electrophilic amination of alkenes and alkynes.

Breakdown of hemiorthothioamide tetrahedral intermediates

1979 ◽  
Vol 44 (4) ◽  
pp. 666-668 ◽  
Author(s):  
Moses K. Kaloustian ◽  
Maria Isabel Aguilar-Laurents de Gutierrez ◽  
Randa B. Nader
Keyword(s):  
Tetrahedral Intermediates

Direct One-Pot Synthesis of α-Siloxy-Weinreb Amides from Aldehydes

2007 ◽  
Vol 72 (25) ◽  
pp. 9850-9853 ◽  
Author(s):  
Hisao Nemoto ◽  
Rujian Ma ◽  
Hideki Moriguchi ◽  
Tomoyuki Kawamura ◽  
Masaki Kamiya ◽  
...  
Keyword(s):  
One Pot ◽  
Weinreb Amides ◽  
One Pot Synthesis

ChemInform Abstract: Highly Stereoselective Cyclopropanation of Diazo Weinreb Amides Catalyzed by Chiral Ru(II)-Amm-Pheox Complexes.

ChemInform ◽  
2016 ◽  
Vol 47 (43) ◽  
Author(s):  
Soda Chanthamath ◽  
Hamada S. A. Mandour ◽  
Thu Minh Thi Tong ◽  
Kazutaka Shibatomi ◽  
Seiji Iwasa
Keyword(s):  
Weinreb Amides

Ruthenium-Catalyzed C–H Oxygenation on Aryl Weinreb Amides

2013 ◽  
Vol 15 (3) ◽  
pp. 718-720 ◽  
Author(s):  
Fanzhi Yang ◽  
Lutz Ackermann
Keyword(s):  
Weinreb Amides
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