ChemInform Abstract: Broensted Acid-Catalyzed Aza Diels-Alder Reaction of Danishefsky′s Diene with Aldimine Generated in situ from Aldehyde and Amine in Aqueous Media.

ChemInform ◽  
2010 ◽  
Vol 31 (4) ◽  
pp. no-no
Author(s):  
Takahiko Akiyama ◽  
Jun Takaya ◽  
Hirotaka Kagoshima
RSC Advances ◽  
2015 ◽  
Vol 5 (72) ◽  
pp. 58798-58803 ◽  
Author(s):  
Wei He ◽  
Zheng Fang ◽  
Zhao Yang ◽  
Dong Ji ◽  
Kai Guo

The first direct aza-Diels–Alder reaction catalyzed using phosphotungstic acid combined with a water absorption device in a micro-flow system was reported.


2000 ◽  
Vol 11 (12) ◽  
pp. 2509-2523 ◽  
Author(s):  
Renée Paugam ◽  
Emmanuelle Valenciennes ◽  
Linda Le Coz-Bardol ◽  
Jean-Christophe Garde ◽  
Lya Wartski ◽  
...  

1995 ◽  
Vol 73 (10) ◽  
pp. 1675-1694 ◽  
Author(s):  
Dennis G. Hall ◽  
Renate Müller ◽  
Pierre Deslongchamps

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.


Tetrahedron ◽  
2008 ◽  
Vol 64 (48) ◽  
pp. 10924-10929 ◽  
Author(s):  
Malihe Javan Khoshkholgh ◽  
Saeed Balalaie ◽  
Rolf Gleiter ◽  
Frank Rominger

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