Montmorillonite K10-Catalyzed Aza Diels-Alder Reaction of Danishefsky’s Diene with Aldimines, Generated in situ from Aliphatic Aldehydes and Amine, in Aqueous Media

Synlett ◽  
2002 ◽  
Vol 2002 (11) ◽  
pp. 1898-1900 ◽  
Author(s):  
Takahiko Akiyama ◽  
Keiichiro Matsuda ◽  
Kohei Fuchibe
Keyword(s):  
Aqueous Media ◽  
Alder Reaction ◽  
Diels Alder ◽  
Aliphatic Aldehydes ◽  
Montmorillonite K10 ◽  
Diels Alder Reaction ◽  
Danishefsky's Diene

Enantioselective Diels–Alder Reaction of 3-Nitrocoumarins Promoted by Chiral Organoammonium Salt Catalysts

Synlett ◽  
2020 ◽  
Vol 31 (20) ◽  
pp. 2013-2017
Author(s):  
Akira Sakakura ◽  
Yudai Fujii ◽  
Ryota Nakao ◽  
Saki Sugihara ◽  
Keita Fujita ◽  
...  
Keyword(s):  
Amino Alcohol ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Danishefsky's Diene

AbstractAn enantioselective Diels–Alder reaction of 3-nitrocoumarins has been developed. A tryptophan-derived C 1-symmetric organoammonium thiourea catalyst promoted the reaction of 3-nitrocoumarins with Danishefsky’s diene to give the corresponding adducts with good enantioselectivity (up to 94% ee). One of the resulting adducts was converted into a chiral carbocyclic quaternary β-amino alcohol.

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.

Intramolecular hetero-Diels–Alder reaction of 1-oxa-1,3-butadienes with terminal acetylenes in aqueous media using CuI

Tetrahedron ◽  
2008 ◽  
Vol 64 (48) ◽  
pp. 10924-10929 ◽  
Author(s):  
Malihe Javan Khoshkholgh ◽  
Saeed Balalaie ◽  
Rolf Gleiter ◽  
Frank Rominger
Keyword(s):  
Aqueous Media ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Terminal Acetylenes

Insights into the stereoselective BF3-catalyzed hetero Diels–Alder reaction of Garner’s aldehyde with Danishefsky’s diene

2010 ◽  
Vol 21 (4) ◽  
pp. 398-404 ◽  
Author(s):  
Carolina Fontana ◽  
Marcelo Incerti ◽  
Guillermo Moyna ◽  
Eduardo Manta
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Danishefsky's Diene
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