“…[17][18][19][20] Since then, there has been an emerging interest in the chemistry of allenamides that ranges from medicinal studies, [21][22][23] to materials using living polymerization, 24 to synthetic methodologies. [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44] These efforts support the notion that allenamides are becoming a proven allenamine-equivalent with the right balance of stability and reactivity.…”
Section: Introduction Of Allenamidesmentioning
confidence: 87%
“…Tanaka 29 and Farina 30 both communicated an elimination protocol for preparations of β-lactam-based α,α-disubstituted allenamides 52 and 53 , respectively, [Scheme ] from enol triflates. These allenamides were specifically designed to access cepham analogues [see below]. , 10 Tanaka and Farina's Eliminations…”
Section: Part I Synthesis Of Allenamidesmentioning
confidence: 99%
“…Allenamides had been studied rarely until recently there were very few reports until 1989. − Since then, there has been an emerging interest in the chemistry of allenamides that ranges from medicinal studies, − to materials using living polymerization, to synthetic methodologies. − These efforts support the notion that allenamides are becoming a proven allenamine-equivalent with the right balance of stability and reactivity.…”
This Account highlights recent studies describing utility of allenamides in stereoselective inter- and intramolecular synthetic methodologies. It is written to raise interest in the chemistry of allenamides.
“…[17][18][19][20] Since then, there has been an emerging interest in the chemistry of allenamides that ranges from medicinal studies, [21][22][23] to materials using living polymerization, 24 to synthetic methodologies. [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44] These efforts support the notion that allenamides are becoming a proven allenamine-equivalent with the right balance of stability and reactivity.…”
Section: Introduction Of Allenamidesmentioning
confidence: 87%
“…Tanaka 29 and Farina 30 both communicated an elimination protocol for preparations of β-lactam-based α,α-disubstituted allenamides 52 and 53 , respectively, [Scheme ] from enol triflates. These allenamides were specifically designed to access cepham analogues [see below]. , 10 Tanaka and Farina's Eliminations…”
Section: Part I Synthesis Of Allenamidesmentioning
confidence: 99%
“…Allenamides had been studied rarely until recently there were very few reports until 1989. − Since then, there has been an emerging interest in the chemistry of allenamides that ranges from medicinal studies, − to materials using living polymerization, to synthetic methodologies. − These efforts support the notion that allenamides are becoming a proven allenamine-equivalent with the right balance of stability and reactivity.…”
This Account highlights recent studies describing utility of allenamides in stereoselective inter- and intramolecular synthetic methodologies. It is written to raise interest in the chemistry of allenamides.
“…Likewise, Tanaka demonstrated that an α-activated Nallenamide favors the 1,4-conjugated addition of secondary amines to the central carbon of the allene, generating key intermediates for the synthesis of 3-substituted cephems. 8 Broggini showed that a base-promoted intramolecular hydroamination takes place under microwave irradiation at the central allenic carbon, allowing the formation of dihydropyrazinones. 9 In none of these related studies have N-allenamides bearing an electron-withdrawing group at the terminal position been used.…”
N-Allenamides, substituted by an ester at the
γ-position, were obtained through addition of terminal ynamides
with ethyl diazoacetate under copper catalysis for the first time.
Regio- and stereoselective hydroamination of those activated N-allenamides provided exclusively E-configured
captodative enamimes through a one-pot anti-Michael addition. Numerous
ynamides as well as various secondary amines were adapted in this
process.
The sections in this article are
Introduction
Reduction
Electrohydrocyclization
Electroreductive Cyclization
Reductive Cyclization of Ketonitriles
Reductive Cyclization of Pyridinium Salts
Vitamin
B
12
‐mediated Cyclizations
Organonickel and Organopalladium Reagents
Oxidation
K
olbe Oxidation
Arene Oxidations
[5 + 2] Cycloadditions to Oxidized Aromatics
Oxidation at and Adjacent to Nitrogen
Concluding Remarks
Acknowledgment
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