Catalytic Enantioselective Michael Additions to Unsaturated Ester Derivatives Using Chiral Copper(II) Lewis Acid Complexes

1999 ◽  
Vol 1 (6) ◽  
pp. 865-868 ◽  
Author(s):  
David A. Evans ◽  
Michael C. Willis ◽  
Jeffrey N. Johnston
Keyword(s):  
Lewis Acid ◽  
Unsaturated Ester ◽  
Michael Additions

Michael Addition of Indoles to Enones Catalyzed by a Cationic Iron Salt

Synthesis ◽  
2021 ◽  
Author(s):  
Takashi Nishikata ◽  
Tsukasa Inishi ◽  
Goki Hirata
Keyword(s):  
Lewis Acid ◽  
Michael Addition ◽  
Iron Catalyst ◽  
Unsaturated Ester ◽  
Iron Salt ◽  
Michael Additions ◽  
The Michael Addition

AbstractIndoles are one of the most valuable nucleophiles in Michael additions catalyzed by a proper Lewis acid. In this paper, we found that a cationic iron salt is effective to carry out the Michael addition of indoles. β-Mono- and disubstituted enones reacted smoothly with indoles under our conditions. The cationic iron catalyst is very active, and the maximum TON was up to 425. Moreover, cationic iron-catalyzed conditions enabled a chemoselective Michael addition of a substrate possessing both enone and α,β-unsaturated ester moieties.

ChemInform Abstract: Lewis Acid-Enhanced Reactivity of α,β-Unsaturated Ester and Amide toward Radical Addition.

ChemInform ◽  
2010 ◽  
Vol 26 (46) ◽  
pp. no-no
Author(s):  
H. URABE ◽  
K. YAMASHITA ◽  
K. SUZUKI ◽  
K. KOBAYASHI ◽  
F. SATO
Keyword(s):  
Lewis Acid ◽  
Radical Addition ◽  
Unsaturated Ester

scholarly journals Origin of Enantioselectivity Reversal in Lewis Acid-Catalyzed Michael Additions Relying on the Same Chiral Source

2020 ◽  
Author(s):  
Paul S. Riehl ◽  
Alistair D. Richardson ◽  
Tatsuhiro Sakamoto ◽  
Jolene P. Reid ◽  
Corinna Schindler
Keyword(s):  
Asymmetric Catalysis ◽  
Lewis Acid ◽  
Chiral Ligand ◽  
Potential Significance ◽  
Kinetics And Thermodynamics ◽  
Important Concept ◽  
Michael Additions ◽  
Acid Catalyzed ◽  
Mechanistic Understanding

Enantiodivergence is an important concept in asymmetric catalysis that enables access to both enantiomers of a product relying on the same chiral source. This strategy is particularly appealing as an alternate approach when only one enantiomer of the required chiral ligand is readily accessible but both enantiomers of the product are desired. Despite their potential significance, general catalytic methods to induce reversal in enantioselectivity remain underdeveloped. Herein we report our studies focused on elucidating the origin of enantioselectivity reversal in Lewis acid-catalyzed Michael additions relying on the same enantiomer of ligand as the chiral source. Our results provide a detailed mechanistic understanding of this transformation based on experimental and computational investigations which reveal the important interplay between kinetics and thermodynamics responsible for the observed enantiodivergence.

scholarly journals Origin of Enantioselectivity Reversal in Lewis Acid-Catalysed Michael Additions Relying on the Same Chiral Source

2021 ◽  
Author(s):  
Corinna Stefanie Schindler ◽  
Paul S. Riehl ◽  
Alistair D Richardson ◽  
Tatsuhiro Sakamoto ◽  
Jolene Reid
Keyword(s):  
Asymmetric Catalysis ◽  
Lewis Acid ◽  
Important Concept ◽  
Michael Additions

Enantiodivergence is an important concept in asymmetric catalysis that enables access to both enantiomers of a product relying on the same chiral source as reagent. This strategy is particularly appealing...

Asymmetric Lewis Acid Catalysis in Water: α-Amino Acids as Effective Ligands in Aqueous Biphasic Catalytic Michael Additions

2009 ◽  
Vol 2009 (6) ◽  
pp. 810-821 ◽  
Author(s):  
Karolina Aplander ◽  
Rui Ding ◽  
Mikhail Krasavin ◽  
U. Marcus Lindström ◽  
Johan Wennerberg
Keyword(s):  
Amino Acids ◽  
Lewis Acid ◽  
Acid Catalysis ◽  
Lewis Acid Catalysis ◽  
Michael Additions ◽  
Aqueous Biphasic

Imidazolium-based polymer supported gadolinium triflate as a heterogeneous recyclable Lewis acid catalyst for Michael additions

2008 ◽  
Vol 49 (21) ◽  
pp. 3466-3470 ◽  
Author(s):  
Ramesh Alleti ◽  
Woon Su Oh ◽  
Meher Perambuduru ◽  
C.V. Ramana ◽  
V. Prakash Reddy
Keyword(s):  
Lewis Acid ◽  
Acid Catalyst ◽  
Michael Additions ◽  
Lewis Acid Catalyst ◽  
Polymer Supported
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