In situ generation and Diels—Alder reaction of benzynes derivatives with 5-membered ring heterocycles using a microcapillary flow reactor

2016 ◽  
Vol 6 (4) ◽  
pp. 293-296 ◽  
Author(s):  
Abir Khadra ◽  
Michael G. Organ
Keyword(s):  
Flow Reactor ◽  
Alder Reaction ◽  
Membered Ring ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
In Situ Generation

Asymmetric Diels–Alder Reaction of 2-Methyl-3-indolylmethanols via in Situ Generation of o-Quinodimethanes

2012 ◽  
Vol 14 (23) ◽  
pp. 5940-5943 ◽  
Author(s):  
You-Cai Xiao ◽  
Qing-Qing Zhou ◽  
Lin Dong ◽  
Tian-Yu Liu ◽  
Ying-Chun Chen
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
In Situ Generation

ChemInform Abstract: Asymmetric Diels-Alder Reaction of 2-Methyl-3-indolylmethanols via in situ Generation of o-Quinodimethanes.

ChemInform ◽  
2013 ◽  
Vol 44 (17) ◽  
pp. no-no
Author(s):  
You-Cai Xiao ◽  
Qing-Qing Zhou ◽  
Lin Dong ◽  
Tian-Yu Liu ◽  
Ying-Chun Chen
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
In Situ Generation

scholarly journals Studies on the transannular Diels–Alder reaction of 15-membered macrocyclic trienes containing a trans-trans diene. Part I: Synthesis and isomerization of various model cyclopentadecatrienes

1995 ◽  
Vol 73 (10) ◽  
pp. 1675-1694 ◽  
Author(s):  
Dennis G. Hall ◽  
Renate Müller ◽  
Pierre Deslongchamps
Keyword(s):  
Aqueous Media ◽  
Alder Reaction ◽  
Membered Ring ◽  
Diels Alder ◽  
Coupling Reactions ◽  
Diels Alder Reaction ◽  
Trans Diene

The transannular Diels–Alder reaction of 15-membered macrocyclic trienes with a trans-trans-cis (TTC) olefin geometry can lead to A.B.C.[6.6.7] tricyclic products of trans-syn-trans (TST) and cis-syn-cis (CSC) stereochemistry whereas the TTT isomers can produce the trans-anti-cis (TAC) and cis-anti-trans (CAT) tricycles. In order to study the influence of the position (pro-6.6 or pro-6.7) and the nature (alkyl, alkoxymethyl, or formyl) of the dienophile substituent, a set of 10 model cyclopentadecatrienes was prepared. The synthesis of appropriately functionalized trisubstituted dienophile and diene synthons, as well as their coupling reactions affording acyclic precursors, is described in this paper (first in a series of two). A mild and efficient macrocyclization protocol yielded the required methyl- or alkoxymethyl-substituted cyclic substrates. Further transformations led to the formyl-substituted ones. In particular, the TTT macrocycles containing an enal as a dienophile could be completely isomerized to the corresponding TTC thermodynamic isomers in acidic aqueous media. Keywords: transannular, Diels–Alder, 15-membered ring, A.B.C.[6.6.7] tricycles, diterpene.

scholarly journals Diels–Alder reactions of myrcene using intensified continuous-flow reactors

2017 ◽  
Vol 13 ◽  
pp. 120-126 ◽  
Author(s):  
Christian H Hornung ◽  
Miguel Á Álvarez-Diéguez ◽  
Thomas M Kohl ◽  
John Tsanaktsidis
Keyword(s):  
Continuous Flow ◽  
Flow Reactor ◽  
Scale Up ◽  
Reaction Times ◽  
Alder Reaction ◽  
Diels Alder ◽  
Flow Reactors ◽  
Diels Alder Reaction ◽  
Naturally Occurring ◽  
Continuous Flow Reactors

This work describes the Diels–Alder reaction of the naturally occurring substituted butadiene, myrcene, with a range of different naturally occurring and synthetic dienophiles. The synthesis of the Diels–Alder adduct from myrcene and acrylic acid, containing surfactant properties, was scaled-up in a plate-type continuous-flow reactor with a volume of 105 mL to a throughput of 2.79 kg of the final product per day. This continuous-flow approach provides a facile alternative scale-up route to conventional batch processing, and it helps to intensify the synthesis protocol by applying higher reaction temperatures and shorter reaction times.

Organocatalytic enantioselective Diels–Alder reaction between hydroxymaleimides and in situ generated nitrosoalkenes for direct preparation of chiral hemiketals with 1,2-oxazine skeleton

2021 ◽  
Author(s):  
Min Xiang ◽  
Chen-Yi Li ◽  
Jian Zhang ◽  
Ying Zou ◽  
Wen-Sheng Li ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Direct Preparation

Organocatalytic Enantioselective IEDDA reaction between hydroxymaleimides and in situ generated nitrosoalkenes has been disclosed, a series of chiral hemiketals containing 5,6-dihydro-4H-l,2-oxazines and succinimide frameworks have been prepared.

scholarly journals A rhodium catalyzed cycloisomerization and tandem Diels–Alder reaction for facile access to diverse bicyclic and tricyclic heterocycles

2019 ◽  
Vol 10 (18) ◽  
pp. 4805-4810 ◽  
Author(s):  
Yirong Zhou ◽  
Ali Nikbakht ◽  
Felix Bauer ◽  
Bernhard Breit
Keyword(s):  
Alder Reaction ◽  
Membered Ring ◽  
Diels Alder ◽  
Catalyst Loading ◽  
Diels Alder Reaction ◽  
Low Catalyst Loading

A rhodium catalyzed cycloisomerization of 1,6-allenenes successfully prepared six-membered ring exocyclic 1,3-dienes. Further tandem Diels–Alder reaction with various dienophiles provided diverse bicyclic and tricyclic heterocycles. This methodology is characterised by complete atom and step economy, low catalyst loading, and excellent chemo-, regio-, and diastereoselectivity.

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