Diastereoselective Synthesis of Morpholine Derivatives from Grignard Reagents and N-Sulfinyl Imines

Synlett ◽  
2021 ◽  
Author(s):  
Eric P. A. Talbot ◽  
Joseph M. Bateman ◽  
Diana Chan ◽  
Mustafa Moroglu ◽  
Benjamin Rahemtulla
Keyword(s):  
Grignard Reagent ◽  
Stereoselective Synthesis ◽  
Grignard Reagents ◽  
Diastereoselective Synthesis ◽  
Step Process ◽  
Diastereoselective Addition ◽  
Morpholine Derivatives

The stereoselective synthesis of C3-substituted morpholine derivatives has been achieved through a two-step process involving diastereoselective addition of a Grignard reagent to a sulfinyl imine, followed by cyclization.

Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (±)-epi-indolizidine 167B and 209D

2014 ◽  
Vol 12 (36) ◽  
pp. 7026-7035 ◽  
Author(s):  
Anil K. Saikia ◽  
Kiran Indukuri ◽  
Jagadish Das
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Cyclization Reaction ◽  
Diastereoselective Synthesis ◽  
Prins Reaction ◽  
Prins Cyclization ◽  
Acyliminium Ions

A diastereoselective synthesis of 4-O-tosyl piperidine containing azabicyclic derivatives has been established via Prins cyclization reaction. This protocol has been applied for the total synthesis of (±)-epi-indolizidine 167B and 209D.

The addition of organometallic reagents to tetramesityldigermene

2002 ◽  
Vol 80 (11) ◽  
pp. 1387-1392 ◽  
Author(s):  
Kyle L Fujdala ◽  
David W.K Gracey ◽  
Erica F Wong ◽  
Kim M Baines
Keyword(s):  
Ligand Exchange ◽  
Grignard Reagent ◽  
Thermal Conditions ◽  
Grignard Reagents ◽  
Ethylmagnesium Bromide ◽  
Organometallic Reagent ◽  
Organometallic Reagents ◽  
Thermal Cleavage

The thermolysis and photolysis of hexamesitylcyclotrigermane in the presence of ethylmagnesium bromide has been investigated. Under photochemical conditions, ethyldimesitylgermane, 1,2-diethyl-1,1,2-trimesityldigermane and ethyl-1,1,2,2-tetramesityldigermane were isolated and, under thermal conditions, 1,2,2-triethyl-1,1-dimesityl digermane and 2,2-diethyl-1,1,1-trimesityldigermane were isolated. The photolysis of hexamesitylcyclotrigermane in the presence of methyllithium has also been investigated. In both cases, the organometallic reagent adds to tetramesityl digermene and dimesitylgermylene formed by photochemical or thermal cleavage of the cyclotrigermane. In the case of the addition of the Grignard reagent, the resulting germyl Grignard reagent undergoes a facile ligand exchange reaction.Key words: digermene, germylene, Grignard reagents, alkyllithium reagents, germylmagnesium compounds, germyllithium compounds.

Grignard reagent formation via C-F bond activation: a centenary perspective

2022 ◽  
Author(s):  
Eunsung Lee ◽  
Ewa Pietrasiak
Keyword(s):  
Bond Dissociation Energy ◽  
Dissociation Energy ◽  
Grignard Reagent ◽  
Bond Activation ◽  
Grignard Reagents ◽  
Bond Dissociation ◽  
High Bond

Examples of Grignard reagents obtained by C-F bond activation with magnesium kept appearing in the literature over the last century. Due to the high bond dissociation energy of the C-F...

Use of Menthyl 2-Methoxynaphthalene-1-sulfinates in the Andersen Synthesis of Optically Active Sulfoxides. Facile Cleavage by Grignard Reagents of Some Aromatic Methyl Ethers

1994 ◽  
Vol 47 (10) ◽  
pp. 1925 ◽  
Author(s):  
KH Bell ◽  
LF Mccaffery
Keyword(s):  
Grignard Reagent ◽  
Methoxy Group ◽  
Optically Active ◽  
Grignard Reagents ◽  
Sulfinyl Group

The pure crystalline diastereomers (1R,2S,5R)-menthyl (R)- and (S)-2-methoxynaphthalene-1-sulfinate (1b) have been prepared and, by reaction with Grignard reagents (the Andersen procedure), converted into optically active alkyl and aryl 2-methoxynaphthyl sulfoxides in 67-77% yields. Use of an excess of Grignard reagent results in facile O-alkyl cleavage of the methoxy group to the corresponding naphthol or a competing loss of the alkyl- or aryl- sulfinyl group to form 2-methoxynaphthalene. Pure diastereomers of menthyl 2,7- dimethoxynaphthalene-1-sulfinate (2b) and menthyl 4-methoxynaphthalene-1-sulfinate (3b) have also been prepared and their reactions with Grignard reagents have been studied.

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