Novel synthesis of a highly functionalized cyclopropane derivative

2003 ◽  
Vol 81 (9) ◽  
pp. 1003-1011 ◽  
Author(s):  
Stéphane Trudeau ◽  
Pierre Deslongchamps
Keyword(s):  
Double Bond ◽  
Inductive Effect ◽  
Acetate Group ◽  
Enol Ether ◽  
Cyclopropane Derivative ◽  
Novel Synthesis ◽  
Model Study ◽  
Silyl Enol Ether ◽  
Ring Structures

A model study was carried out to explore the feasibility of synthesizing fused tricyclic ring structures containing a C7—C8 double bond juncture (steroid numbering) by employing an SN2' cyclization of a silyl enol ether to displace an allylic acetate as the key step. Instead of the anticipated product, highly functionalized cyclopropanes were obtained. These novel cyclopropane structures are the result of the concomitant 1,2-migration of a dithiane thioether moiety and the eventual displacement of the acetate group, followed by the cyclization of the silyl enol ether.Key words: tricycles, SN2' cyclization, inductive effect, cyclopropane.

Synthesis of α-Arylcarboxylic Acid Amides from Silyl Enol Ether via Migratory Amidation with 2-Azido-1,3-dimethylimidazolinium Hexafluorophosphate

2013 ◽  
Vol 42 (7) ◽  
pp. 691-693 ◽  
Author(s):  
Mitsuru Kitamura ◽  
Kento Murakami ◽  
Yuichiro Shiratake ◽  
Tatsuo Okauchi
Keyword(s):  
Enol Ether ◽  
Silyl Enol Ether

Reactions with 4-Thiohydantoin. Preparation of 5-Arylidene-4-Thiohydantoin, their Reactions towards Grignard Reagents and the Alkylating Agents

1974 ◽  
Vol 29 (1-2) ◽  
pp. 99-103 ◽  
Author(s):  
A. F. A. Shalaby ◽  
H. A. Daboun ◽  
S. S. M. Boghdadi
Keyword(s):  
Double Bond ◽  
Alkylating Agents ◽  
Aromatic Aldehydes ◽  
Grignard Reagents ◽  
Cyclopropane Derivative ◽  
Ethereal Diazomethane

4-Thiohydantoin and 1-phenyl-4-thiohydantoin reacted with aromatic aldehydes to give the corresponding 5-arylidene-4-thiohydantoin (1 a-h). la was obtained also from 5-benzylidene hydantoin and phosphorous pentasulphide. Grignard reagents added to the lateral double bond of (1 a-c) to give after hydrolysis the colorless products 3. Treatment of (1a, b) with alkylating agents gave the corresponding alkylmercapto derivatives (4 a-h). Also (4a, e) were obtained by the action of ethereal diazomethane on (1a, b). By further methylation of (4 e) with diazomethane, a cyclopropane derivative could be isolated.

Carbon-carbon bond formation in reactions of PhIO.cntdot.HBF4-silyl enol ether adduct with alkenes or silyl enol ethers

1989 ◽  
Vol 54 (11) ◽  
pp. 2605-2608 ◽  
Author(s):  
V. V. Zhdankin ◽  
M. Mullikin ◽  
Rik Tykwinski ◽  
Bruce Berglund ◽  
Ronald Caple ◽  
...  
Keyword(s):  
Bond Formation ◽  
Enol Ether ◽  
Enol Ethers ◽  
Carbon Bond ◽  
Silyl Enol Ethers ◽  
Carbon Carbon Bond ◽  
Silyl Enol Ether

An Access to Highly Enantioenriched cis-3,5-Disubstituted γ-Lactones from α-Bromoacetate and Silyl Enol Ether

2021 ◽  
Author(s):  
Ha Rim Lee ◽  
Seo Yun Kim ◽  
Min Ji Park ◽  
Yong Sun Park
Keyword(s):  
Nucleophilic Substitution ◽  
Enol Ether ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Synthetic Strategy ◽  
Silyl Enol Ether

A novel synthetic strategy for highly enantioenriched cis-3,5-disubstituted γ-lactones has been developed by the AgOTf-promoted nucleophilic substitution of α-bromoacetates with silyl enol ethers and subsequent reductive lactonization. The utility of...

Novel synthesis of N,N-diprotected amino acids by alkylation of imidodicarbonates. A model study

Peptides 1990 ◽  
1991 ◽  
pp. 19-20 ◽  
Author(s):  
Fredrik Degerbeck ◽  
Bengt Fransson ◽  
Leif Grehn ◽  
Ulf Ragnarsson
Keyword(s):  
Amino Acids ◽  
Novel Synthesis ◽  
Model Study

Silyl Enol Ether Based Nucleophiles

2012 ◽  
pp. 1
Author(s):  
D. W. C. MacMillan ◽  
A. J. B. Watson
Keyword(s):  
Enol Ether ◽  
Silyl Enol Ether
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