- A mild ligand-free iron-catalyzed liberation of alcohols from allylcarbonates
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Different from most carbonates the allyloxy carbonyl protecting group can be cleaved under neutral conditions using metal catalysis. However, most of the catalysts employed to date are based upon precious metals. Herein we present two protocols for the mild Fe-catalyzed liberation of alcohols from allylcarbonates that are characterized by broad functional group tolerance and exclusive chemoselectivity.
- Dieskau, Andre P.,Plietker, Bernd
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supporting information; experimental part
p. 5544 - 5547
(2011/12/05)
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- Regioselective iron-catalyzed decarboxylative allylic etherification
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[Chemical Equation Presented] An anionic iron complex catalyzes the decarboxylative allylation of phenols to form allylic ethers in high yield. The allylation is regioselective rather than regiospecific. This suggests that the allylation proceeds through π-allyl iron intermediates in contrast to related allylations of carbon nucleophiles that have been proposed to proceed via π-allyl complexes. Ultimately, iron catalysts have the potential to replace more expensive palladium catalysts that are typically utilized for decarboxylative couplings.
- Trivedi, Rushi,Tunge, Jon A.
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supporting information; experimental part
p. 5650 - 5652
(2010/02/28)
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- Expanding the scope and orthogonality of PNA synthesis
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Peptide nucleic acids (PNAs) hybridize to natural oligonucleotides according to Watson and Crick base-pairing rules. The robustness of PNA oligomers and ease of synthesis have made them an attractive platform to encode small or macromolecules for microarr
- Pothukanuri, Srinivasu,Pianowski, Zbigniew,Winssinger, Nicolas
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supporting information; experimental part
p. 3141 - 3148
(2009/05/27)
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- Enzymatic resolution of a secondary amine using novel acylating reagents
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Phenyl allylcarbonates are useful acylating agents for the enzymatic resolution of 1-methyl tetrahydroisoquinoline.
- Breen, Gary F.
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p. 1427 - 1430
(2007/10/03)
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- A bimetallic catalyst and dual role catalyst: Synthesis of N-(alkoxycarbonyl)indoles from 2-(alkynyl)phenylisocyanates
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3-Allyl-N-(alkoxycarbonyl)indoles are synthesized via the reaction of 2-(alkynyl)phenylisocyanates and allyl carbonates in the presence of Pd(PPh3)4 (1 mol %) and CuCl (4 mol %) bimetallic catalyst. It is most probable that Pd0
- Kamijo, Shin,Yamamoto, Yoshinori
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p. 4764 - 4771
(2007/10/03)
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- Selective synthesis of carbamate protected polyamines using alkyl phenyl carbonates
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Utilising alkyl phenyl carbonates, an economical, practical and versatile method for selective Boc, Cbz and Alloc protection of polyamines has been developed. This method allows Boc, Cbz and Alloc protection of primary amines in the presence of secondary amines by reaction of the polyamines with the alkyl phenyl carbonates. Also, this method allows mono carbamate protection of simple symmetrical aliphatic α,ω-alkanediamines in high yields with respect to the diamine. Finally, the method allows selective carbamate protection of a primary amine located on a primary carbon in the presence of a primary amine located on a secondary or a tertiary carbon in excellent yields.
- Pittelkow, Michael,Lewinsky, Rasmus,Christensen, Jorn Bolstad
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p. 2195 - 2202
(2007/10/03)
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- Derivatives of N-HALS-substituted amic acid hydrazides
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N-(2,2,6,6-tetraalkyl-4-piperidinyl)amic acid hydrazides contain a light stabilizing group, a heat stabilizing group and an amic acid hydrazide functionality in the same molecule. The amic acid hydrazide functionality in the compounds enhances the photoox
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- Synthesis of allylic aryl ethers via palladium-catalyzed decarboxylation of allylic aryl carbonates
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Allylic aryl ethers are readily prepared in high yield by the palladium-catalyzed decarboxylation of allylic aryl carbonates.
- Larock,Lee
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p. 6315 - 6318
(2007/10/02)
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