Enantioselective palladium catalyzed conjugate additions of ortho-substituted arylboronic acids to β,β-disubstituted cyclic enones: total synthesis of herbertenediol, enokipodin A and enokipodin B

2014 ◽  
Vol 12 (31) ◽  
pp. 5883-5890 ◽  
Author(s):  
Jeffrey Buter ◽  
Renée Moezelaar ◽  
Adriaan J. Minnaard
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Conjugate Addition ◽  
Natural Product Synthesis ◽  
Conjugate Additions ◽  
Arylboronic Acids ◽  
Cyclic Enones ◽  
Palladium Catalyzed

Palladium catalyzed asymmetric conjugate addition of ortho-substituted arylboronic acids to cyclic enones and its application in natural product synthesis.

scholarly journals Synthesis of diverse β-quaternary ketones via palladium-catalyzed asymmetric conjugate addition of arylboronic acids to cyclic enones

Tetrahedron ◽  
2015 ◽  
Vol 71 (35) ◽  
pp. 5781-5792 ◽  
Author(s):  
Jeffrey C. Holder ◽  
Emmett D. Goodman ◽  
Kotaro Kikushima ◽  
Michele Gatti ◽  
Alexander N. Marziale ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Arylboronic Acids ◽  
Cyclic Enones ◽  
Palladium Catalyzed

ChemInform Abstract: Synthesis of Diverse β-Quaternary Ketones via Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Cyclic Enones.

ChemInform ◽  
2015 ◽  
Vol 46 (48) ◽  
pp. no-no
Author(s):  
Jeffrey C. Holder ◽  
Emmett D. Goodman ◽  
Kotaro Kikushima ◽  
Michele Gatti ◽  
Alexander N. Marziale ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Arylboronic Acids ◽  
Cyclic Enones ◽  
Palladium Catalyzed

Diastereoselective Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to α-Substituted Cyclic Enones

Synlett ◽  
2017 ◽  
Vol 28 (20) ◽  
pp. 2829-2832 ◽  
Author(s):  
Ang Gao ◽  
Xiu-Yan Liu ◽  
Chang-Hua Ding ◽  
Xue-Long Hou
Keyword(s):  
Conjugate Addition ◽  
Arylboronic Acids ◽  
Mechanistic Investigation ◽  
Cyclic Enones ◽  
Palladium Catalyzed

A palladium-catalyzed conjugate addition of arylboronic acids to α-substituted cyclic enones was developed to give α,β-disubstituted ketones with high diastereoselectivity. Mechanistic investigation showed that the high diastereoselectivity was realized through epimerization.

scholarly journals Mechanistic analysis of an asymmetric palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones

2015 ◽  
Vol 6 (3) ◽  
pp. 1917-1922 ◽  
Author(s):  
Cornelia L. Boeser ◽  
Jeffrey C. Holder ◽  
Buck L. H. Taylor ◽  
K. N. Houk ◽  
Brian M. Stoltz ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Addition Reaction ◽  
Desorption Electrospray Ionization ◽  
Conjugate Addition ◽  
Arylboronic Acids ◽  
Mechanistic Insight ◽  
Mechanistic Analysis ◽  
Cyclic Enones ◽  
Palladium Catalyzed ◽  
Insight Into

Mechanistic insight into a Pd-catalyzed conjugate addition reaction was gained using desorption electrospray ionization coupled to mass spectrometry.

scholarly journals Construction of all-carbon quaternary stereocenters by catalytic asymmetric conjugate addition to cyclic enones in natural product synthesis

2020 ◽  
Vol 7 (22) ◽  
pp. 3815-3841
Author(s):  
Zhuo Wang
Keyword(s):  
Natural Product ◽  
Conjugate Addition ◽  
Natural Product Synthesis ◽  
Cyclic Enones ◽  
Catalytic Asymmetric ◽  
Quaternary Stereocenters

This review discusses the construction of all-carbon quaternary stereocenters using catalytic asymmetric conjugate addition and its application in natural product synthesis.

Palladium-catalyzed cascade cyclizations involving C–C and C–X bond formation: strategic applications in natural product synthesis

2021 ◽  
Author(s):  
K. R. Holman ◽  
A. M. Stanko ◽  
S. E. Reisman
Keyword(s):  
Natural Product ◽  
Bond Formation ◽  
Natural Product Synthesis ◽  
Cascade Cyclizations ◽  
Palladium Catalyzed ◽  
Multiple Rings

This tutorial review highlights the use of palladium-catalyzed cascade cyclizations in natural product synthesis, focusing on cascades that construct multiple rings and form both C–C and C–X (X = O, N) bonds in a single synthetic operation.

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