ChemInform Abstract: Ligand-Assisted Asymmetric Synthesis. Part 1. Chiral Auxiliaries for the Enantioselective Diels-Alder Reaction.

ChemInform ◽  
2010 ◽  
Vol 23 (30) ◽  
pp. no-no
Author(s):  
J.-L. GRAS ◽  
H. PELLISSIER
Keyword(s):  
Asymmetric Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Auxiliaries ◽  
Diels Alder Reaction

Synthesis and evaluation of 7-hydroxyindan-1-one-derived chiral auxiliaries

2005 ◽  
Vol 83 (5) ◽  
pp. 413-419 ◽  
Author(s):  
Arun A Narine ◽  
Peter D Wilson
Keyword(s):  
Asymmetric Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Auxiliaries ◽  
Diels Alder Reaction ◽  
High Degree

A series of novel chiral acetals were prepared from 7-hydroxyindan-1-one and a variety of substituted chiral nonracemic C2-symmetric 1,2-ethanediols (R = Me, Ph, CH2OMe, CH2OBn, CH2O(1-Np), and i-Pr). These acetals were evaluated as chiral auxiliaries for use in asymmetric synthesis. A high degree of stereochemical induction was observed in the diethylaluminum chloride-promoted Diels–Alder reaction of an acrylate derivative (R = i-Pr) with cyclopentadiene (91:9 dr). This demonstrated that these acetals could serve as effective chiral directors in asymmetric substrate-directed reactions.Key words: 7-hydroxyindan-1-one, chiral nonracemic C2-symmetric 1,2-diols, acetals, chiral auxiliaries, Diels–Alder reaction.

Asymmetric Synthesis of Fused Tetrahydroquinolines via Intramolecular Aza-Diels-Alder Reaction of ortho-Quinone Methide Imines

Synthesis ◽  
2021 ◽  
Author(s):  
Fabian Hofmann ◽  
Cornelius Gärtner ◽  
Martin Kretzschmar ◽  
Christoph Schneider
Keyword(s):  
Asymmetric Synthesis ◽  
Alder Reaction ◽  
Single Step ◽  
Diels Alder ◽  
Quinone Methide ◽  
Bronsted Acid ◽  
Atom Economy ◽  
Diels Alder Reaction ◽  
Brönsted Acid ◽  
Chiral Bronsted Acid

Aza-Diels Alder reactions are straightforward processes in the construction of N-heterocycles, featuring inherent atom-economy and stereospecificity. Intramolecular strategies allow formation of bicyclic core structures with up to three stereocenters within a single step. Herein, this concept is combined with the chemistry of chiral Brønsted acid-bound ortho-quinone methide imines generating a range of interesting fused tetrahydro-quinolines in a diastereo- and enantioselective manner.

Asymmetric synthesis of N-phenylethyl-2-phenyldecahydroquinolin-4-ones via Lewis acid catalyzed imino-Diels–Alder reaction

2000 ◽  
Vol 11 (12) ◽  
pp. 2509-2523 ◽  
Author(s):  
Renée Paugam ◽  
Emmanuelle Valenciennes ◽  
Linda Le Coz-Bardol ◽  
Jean-Christophe Garde ◽  
Lya Wartski ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Lewis Acid ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Acid Catalyzed

Asymmetric synthesis of isoquinuclidines by Diels–Alder reaction of 1,2-dihydropyridine utilizing a chiral Lewis acid catalyst

Tetrahedron ◽  
2012 ◽  
Vol 68 (6) ◽  
pp. 1774-1781 ◽  
Author(s):  
Chigusa Seki ◽  
Masafumi Hirama ◽  
N.D.M. Romauli Hutabarat ◽  
Junko Takada ◽  
Chonticha Suttibut ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Lewis Acid ◽  
Acid Catalyst ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Chiral Lewis Acid ◽  
Lewis Acid Catalyst

Asymmetric Synthesis of 3,3′-Piperidinoyl Spirooxindoles and Discovery of Stereospecific Cycloadducts as Novel Hedgehog Pathway Modulators

Synthesis ◽  
2020 ◽  
Vol 52 (21) ◽  
pp. 3140-3152
Author(s):  
Kamal Kumar ◽  
Mohammad Rehan ◽  
Jana Flegel ◽  
Franziska Heitkamp ◽  
Jorgelina L. Pergomet ◽  
...  
Keyword(s):  
Transition Metal ◽  
Small Molecules ◽  
Asymmetric Synthesis ◽  
Natural Product ◽  
Transition Metal Complexes ◽  
Alder Reaction ◽  
Diels Alder ◽  
Hedgehog Pathway ◽  
Diels Alder Reaction ◽  
Efficient Access

An enantioselective hetero-Diels–Alder reaction of alkylidene­ oxindoles and 2-aza-3-silyloxy-1,3-butadienes, catalyzed by divalent transition metal complexes with N,N′-dioxide ligands offered an efficient access to natural-product-based 3,3′-piperidinoyl spiroox­indole class of small molecules. exo-Cycloadducts formed via stereospecific cycloaddition with Z-olefin displayed potent activity in modulation of hedgehog pathway.

ChemInform Abstract: Asymmetric Synthesis of the Key Intermediate (VII) of an SP Antagonist RPR 107880 (VIII) Using a Base-Catalyzed Diels-Alder Reaction.

ChemInform ◽  
2000 ◽  
Vol 31 (37) ◽  
pp. no-no
Author(s):  
Hiroaki Okamura ◽  
Hideki Shimizu ◽  
Yasuko Nakamura ◽  
Tetsuo Iwagawa ◽  
Munehiro Nakatani
Keyword(s):  
Asymmetric Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction
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