Hydrogen bonding in alcohols: its effect on the carbene insertion reaction

1982 ◽  
Vol 104 (20) ◽  
pp. 5549-5551 ◽  
Author(s):  
D. Griller ◽  
M. T. H. Liu ◽  
J. C. Scaiano
Keyword(s):  
Hydrogen Bonding ◽  
Insertion Reaction ◽  
Carbene Insertion

scholarly journals Organocatalytic Asymmetric Synthesis of α-Amino Esters from Sulfoxonium Ylides

2021 ◽  
Author(s):  
Wengang Guo ◽  
Hai Huang ◽  
Jianwei Sun
Keyword(s):  
Asymmetric Synthesis ◽  
Insertion Reaction ◽  
Metal Catalyst ◽  
Insertion Reactions ◽  
Amino Esters ◽  
Carbene Insertion

Described here is the first organocatalytic asymmetric N−H insertion reaction of α-carbonyl sulfoxonium ylides. Without a metal catalyst, this reaction represents an attractive complement to the well-established carbene insertion reactions....

A stereocontrolled, enantiomerically specific total synthesis of thienamycin

1980 ◽  
Vol 289 (1036) ◽  
pp. 191-195 ◽  
Keyword(s):  
Total Synthesis ◽  
Aspartic Acid ◽  
Ring System ◽  
Insertion Reaction ◽  
Carbene Insertion ◽  
Metal Catalyzed

A versatile stereocontrolled total synthesis of thienamycin starting from L-aspartic acid is reported. Stereocontrol is achieved by potassium tri- sec -butylborohydride reduction of a thermodynamically formed 3α-acetylazetidinone intermediate. The key [3.2.0] bicyclic ring system is prepared by a metal catalyzed carbene insertion reaction.

scholarly journals A NOVEL, CYCLOBUTANONE-FORMING CARBENE INSERTION REACTION. TETRACYCLO[7.3.1.02,5.05,10]TRIDECAN-4-ONE FROM 1-(TRICYCLO[5.3.1.03,8]UNDEC-3-YL)-2-DIAZOETHAN-1-ONE

1975 ◽  
Vol 4 (9) ◽  
pp. 957-960 ◽  
Author(s):  
Naotake Takaishi ◽  
Yoshiaki Fujikura ◽  
Yoshiaki Inamoto ◽  
Hiroshi Ikeda
Keyword(s):  
Insertion Reaction ◽  
Carbene Insertion

Three-Component Carbene-Insertion Reaction Leading to Allylic Amines

Synfacts ◽  
2007 ◽  
Vol 2007 (7) ◽  
pp. 0749-0749
Author(s):  
D. Van Vranken ◽  
S. Devine
Keyword(s):  
Insertion Reaction ◽  
Allylic Amines ◽  
Carbene Insertion

scholarly journals Synthesis, Electrochemical and Spectroscopic Characterization of Selected Quinolinecarbaldehydes and Their Schiff Base Derivatives

Molecules ◽  
2020 ◽  
Vol 25 (9) ◽  
pp. 2053
Author(s):  
Jakub Wantulok ◽  
Marcin Szala ◽  
Andrea Quinto ◽  
Jacek E. Nycz ◽  
Stefania Giannarelli ◽  
...  
Keyword(s):  
Schiff Base ◽  
Spectroscopic Characterization ◽  
Insertion Reaction ◽  
Synthesis Methods ◽  
X Ray Diffraction ◽  
Oxidation Potentials ◽  
Schiff Base Derivatives ◽  
Carbene Insertion ◽  
Hydroxy Quinoline

A new approach to the synthesis of selected quinolinecarbaldehydes with carbonyl groups located at C5 and/or in C7 positions is presented in this paper in conjunction with spectroscopic characterization of the products. The classical Reimer-Tiemann, Vilsmeier-Haack and Duff aldehyde synthesis methods were compared due to their importance. Computational studies were carried out to explain the preferred selectivity of the presented formylation transformations. A carbene insertion reaction based on Reimer-Tiemann methodology is presented for making 7-bromo-8-hydroxyquinoline-5-carbaldehyde. Additionally, Duff and Vilsmeier-Haack reactions were used in the double formylation of quinoline derivatives and their analogues benzo[h]quinolin-10-ol, 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde, 8-(dimethylamino) quinoline-5,7-dicarbaldehyde and 10-hydroxybenzo[h]quinoline-7,9-dicarbaldehyde. Four Schiff base derivatives of 2,6-diisopropylbenzenamine were prepared from selected quinoline-5-carbaldehydes and quinoline-7-carbaldehyde by an efficient synthesis protocol. Their properties have been characterized by a combination of several techniques: MS, HRMS, GC-MS, FTIR, electronic absorption spectroscopy and multinuclear NMR. The electrochemical properties of 8-hydroxy-quinoline-5-carbaldehyde, 6-(dimethylamino)quinoline-5-carbaldehyde and its methylated derivative were investigated, and a strong correlation between the chemical structure and obtained reduction and oxidation potentials was found. The presence of a methyl group facilitates oxidation. In contrast, the reduction potential of methylated compounds was more negative comparing to non-methylated structure. Calculations of frontier molecular orbitals supported the finding. The structures of 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde and four Schiff bases were determined by single-crystal X-ray diffraction measurements.

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