ChemInform Abstract: Iridium-Catalyzed Allylic Alkylation of Monosubstituted Allylic Acetates with Azlactone, and Separation of Diastereoisomers by Sequential Aza-Cope Rearrangement.

ChemInform ◽  
2012 ◽  
Vol 43 (8) ◽  
pp. no-no
Author(s):  
Motoi Kawatsura ◽  
Hiroaki Tsuji ◽  
Kenta Uchida ◽  
Toshiyuki Itoh
Keyword(s):  
Cope Rearrangement ◽  
Allylic Alkylation

Enantioselective iridium catalyzed α-alkylation of azlactones by a tandem asymmetric allylic alkylation/aza-Cope rearrangement

2019 ◽  
Vol 55 (39) ◽  
pp. 5547-5550 ◽  
Author(s):  
Xue-Dan Bai ◽  
Qing-Feng Zhang ◽  
Ying He
Keyword(s):  
Cope Rearrangement ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation ◽  
Iridium Catalysis

An enantioselective and regioselective α-alkylation of azlactones was developed by iridium catalysis using asymmetric allylic alkylation.

scholarly journals Direct C(sp3)-H allylation of 2-alkylpyridines with Morita-Baylis-Hillman carbonates via a tandem nucleophilic substitution/aza-Cope rearrangement

2021 ◽  
Author(s):  
Siyu Wang ◽  
Lianyou Zheng ◽  
Shutao Wang ◽  
Shulin Ning ◽  
Zhuoqi Zhang ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Cope Rearrangement ◽  
Allylic Alkylation ◽  
Catalyst Free ◽  
Simple Strategy ◽  
Plausible Mechanism ◽  
Mechanism Of The Reaction

A base- and catalyst-free C(sp3) – H allylic alkylation of 2-alkylpyridines with Morita-Baylis-Hillman (MBH) carbonates was described. A plausible mechanism of the reaction might involve a tandem SN2’ type nucleophilic substitution followed by an aza-Cope rearrangement. Various alkyl substituents on 2-alkylpyridines were tolerated in the reaction to give the allylation products in 26-91% yields. The developed method provides a straightforward and operational simple strategy for the allylic functionalization of 2-alkypyridine derivatives.

scholarly journals Correction: Enantioselective iridium catalyzed α-alkylation of azlactones by a tandem asymmetric allylic alkylation/aza-Cope rearrangement

2020 ◽  
Vol 56 (4) ◽  
pp. 663-663
Author(s):  
Xue-Dan Bai ◽  
Qing-Feng Zhang ◽  
Ying He
Keyword(s):  
Cope Rearrangement ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation

Correction for ‘Enantioselective iridium catalyzed α-alkylation of azlactones by a tandem asymmetric allylic alkylation/aza-Cope rearrangement’ by Xue-Dan Bai et al., Chem. Commun., 2019, 55, 5547–5550.

scholarly journals Enantioselective γ-Alkylation of α,β-Unsaturated Malonates and Ketoesters by a Sequential Ir-Catalyzed Asymmetric Allylic Alkylation/Cope Rearrangement

2016 ◽  
Vol 138 (16) ◽  
pp. 5234-5237 ◽  
Author(s):  
Wen-Bo Liu ◽  
Noriko Okamoto ◽  
Eric J. Alexy ◽  
Allen Y. Hong ◽  
Kristy Tran ◽  
...  
Keyword(s):  
Cope Rearrangement ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation

Iridium-catalysed asymmetric allylic alkylation of benzofuran γ-lactones followed by heteroaromatic Cope rearrangement: study of an unusual reaction sequence

2017 ◽  
Vol 53 (36) ◽  
pp. 4997-5000 ◽  
Author(s):  
Maxence Bos ◽  
Emmanuel Riguet
Keyword(s):  
Unusual Reaction ◽  
Cope Rearrangement ◽  
Allylic Alkylation ◽  
Reaction Sequence ◽  
Asymmetric Allylic Alkylation

The iridium-catalysed asymmetric allylic alkylation of benzofuran γ-lactones produces 1,5-hexadienes that were found to be excellent substrates for an unusual heteroaromatic Cope rearrangement.

Synthesis of 7-Membered Ring Carbocycles via a Palladium-Catalyzed Intramolecular Allylic Alkylation-Isomerization-Cope Rearrangement Cascade

2018 ◽  
Vol 2018 (22) ◽  
pp. 2836-2840 ◽  
Author(s):  
Kazuki Tsuruda ◽  
Takahisa Tokumoto ◽  
Naoya Inoue ◽  
Masaya Nakajima ◽  
Tetsuhiro Nemoto
Keyword(s):  
Membered Ring ◽  
Cope Rearrangement ◽  
Allylic Alkylation ◽  
Palladium Catalyzed

scholarly journals Direct C(sp3)–H allylation of 2-alkylpyridines with Morita–Baylis–Hillman carbonates via a tandem nucleophilic substitution/aza-Cope rearrangement

2021 ◽  
Vol 17 ◽  
pp. 2505-2510
Author(s):  
Siyu Wang ◽  
Lianyou Zheng ◽  
Shutao Wang ◽  
Shulin Ning ◽  
Zhuoqi Zhang ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Cope Rearrangement ◽  
Allylic Alkylation ◽  
Catalyst Free ◽  
Simple Strategy ◽  
Plausible Mechanism ◽  
Mechanism Of The Reaction

A base- and catalyst-free C(sp3)–H allylic alkylation of 2-alkylpyridines with Morita–Baylis–Hillman (MBH) carbonates is described. A plausible mechanism of the reaction might involve a tandem SN2’ type nucleophilic substitution followed by an aza-Cope rearrangement. Various alkyl substituents on 2-alkylpyridines were tolerated in the reaction to give the allylation products in 26–91% yields. The developed method provides a straightforward and operational simple strategy for the allylic functionalization of 2-alkypyridine derivatives.

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