Improved Total Synthesis of Indolizidine and Quinolizidine Alkaloids via Nickel-Catalyzed (4+ 2) Cycloaddition
J Renner, SR Smith, JM Cowley… - The Journal of Organic …, 2022 - ACS Publications
A Ni-catalyzed (4+ 2) cycloaddition of bicyclic 3-azetidinones and alkynes was developed to
access indolizidine and quinolizidine alkaloids. A key element was the development of a …
access indolizidine and quinolizidine alkaloids. A key element was the development of a …
Total Synthesis of Indolizidine Alkaloids via Nickel-Catalyzed (4+ 2) Cyclization
J Renner, A Thakur, PM Rutz, JM Cowley… - Organic …, 2020 - ACS Publications
A Ni-catalyzed (4+ 2) cycloaddition of alkynes and azetidinones toward piperidinones was
used as key reaction in the enantioselective synthesis of naturally occurring indolizidine …
used as key reaction in the enantioselective synthesis of naturally occurring indolizidine …
Regioselective Synthesis of 3-Hydroxy-4, 5-alkyl-Substituted Pyridines Using 1, 3-Enynes as Alkynes Surrogates
The poor regioselectivity of the [4+ 2] cycloaddition of 3-azetidinones with internal alkynes
bearing two alkyl substituents via nickel-catalyzed carbon–carbon activation is addressed …
bearing two alkyl substituents via nickel-catalyzed carbon–carbon activation is addressed …
An in Situ Approach to Nickel-Catalyzed Cycloaddition of Alkynes and 3-Azetidinones
A Thakur, JL Evangelista, P Kumar… - The Journal of Organic …, 2015 - ACS Publications
An efficient and convenient procedure that generates the active Ni (0) catalyst in situ from
cheap, air stable Ni (II) precursors is developed for the [4+ 2]-cycloaddition of alkynes and 3 …
cheap, air stable Ni (II) precursors is developed for the [4+ 2]-cycloaddition of alkynes and 3 …
Formal aza-[3+ 3] versus aza-[3+ 2] cycloadditions of heterocyclic enaminones with maleic anhydride and maleimides: skeletally diverse synthesis of pyrrolizidinones …
S Cunha, AO Santos, JTM Correia, JR Sabino - Tetrahedron, 2014 - Elsevier
The domino aza-annulation of cyclic enaminones with maleic anhydride and maleimides
was investigated, and selectively one-step skeletally diverse synthesis of each alkaloid-like …
was investigated, and selectively one-step skeletally diverse synthesis of each alkaloid-like …
Multi-component cycloaddition approaches in the catalytic asymmetric synthesis of alkaloid targets
S Perreault, T Rovis - Chemical Society Reviews, 2009 - pubs.rsc.org
Cycloaddition reactions are attractive strategies for the rapid formation of molecular
complexity in organic synthesis, as multiple bonds are formed in a single process. To this …
complexity in organic synthesis, as multiple bonds are formed in a single process. To this …
Alkaloid-catalyzed enantioselective [3+ 2] cycloaddition of ketenes and azomethine imines
A new asymmetric synthesis of bicyclic pyrazolidinones through an alkaloid-catalyzed formal
[3+ 2] cycloaddition of in situ generated ketenes and azomethine imines is described. The …
[3+ 2] cycloaddition of in situ generated ketenes and azomethine imines is described. The …
Umpolung Chemo-and Regioselective Cascade Addition of Diethylzinc to α-Diketones Followed by Intramolecular Michael Reaction: Stereoselective Synthesis of …
Herein we report an efficient stereoselective umpolung 1, 2-addition of Et2Zn onto α-
diketones followed by intramolecular cascade Michael cyclization. This strategy effectively …
diketones followed by intramolecular cascade Michael cyclization. This strategy effectively …
Intramolecular formal aza-[3+ 3] cycloaddition approach to indoloquinolizidine alkaloids. A stereoselective total synthesis of (±)-tangutorine
S Luo, CA Zificsak, RP Hsung - Organic Letters, 2003 - ACS Publications
A 19-step stereoselective total synthesis of (±)-tangutorine is described here. The total
synthesis features an intramolecular aza-[3+ 3] formal cycloaddition strategy and also a …
synthesis features an intramolecular aza-[3+ 3] formal cycloaddition strategy and also a …
Synthesis of Four‐Membered Aza‐Heterocycles through Catalytic [2+ 2] Cycloaddition Reactions Assisted by Metal Complexes
A Prieto - Synthetic Approaches to Nonaromatic Nitrogen …, 2020 - Wiley Online Library
Summary Azetidine and, more notably, 2‐azetidinone ring systems are found in a large
number of compounds with remarkable biological and pharmacological properties. Among …
number of compounds with remarkable biological and pharmacological properties. Among …