An Expedient Route for the Stereoselective Construction of Bridged Polyheterocyclic Ring Systems Using the Tandem “Pincer” Diels−Alder Reaction

1997 ◽  
Vol 62 (13) ◽  
pp. 4418-4427 ◽  
Author(s):  
Mark Lautens ◽  
Eric Fillion
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Ring Systems ◽  
Diels Alder Reaction

Efficient and regioselective synthesis of bridged ring systems by domino Knoevenagel – hetero-Diels–Alder reaction

2001 ◽  
Vol 79 (11) ◽  
pp. 1511-1514 ◽  
Author(s):  
Lutz F Tietze ◽  
Christian Ott ◽  
Frank Haunert
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Regioselective Synthesis ◽  
Domino Reaction ◽  
Knoevenagel Reaction ◽  
Transition Structure ◽  
Ring Systems ◽  
Contrast Reaction ◽  
Diels Alder Reaction

The bridged heterocycles 10–12 were efficiently prepared by a domino Knoevenagel – hetero-Diels–Alder reaction of N,N'-dimethylbarbituric acid 2 and the aldehydes 6–8 which contain an allyl moiety as dienophile. In contrast, reaction of 2 and aldehyde 5 with a dimethylallyl moiety leads to the annulated product 9. For the formation of 10–12, an exo-Z-syn and for that of 9 an endo-E-syn transition structure is proposed.Key words: bridged compounds, domino reaction, Diels–Alder reaction, heterocycles, Knoevenagel reaction.

scholarly journals Design and synthesis of polycyclic sulfones via Diels–Alder reaction and ring-rearrangement metathesis as key steps

2015 ◽  
Vol 11 ◽  
pp. 1373-1378 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Rama Gunta
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Ring Systems ◽  
Design And Synthesis ◽  
Synthetic Strategy ◽  
Diels Alder Reaction ◽  
Fused Ring ◽  
Materials Used ◽  
Key Steps

Here, we describe a new and simple synthetic strategy to various polycyclic sulfones via Diels–Alder reaction and ring-rearrangement metathesis (RRM) as the key steps. This approach delivers tri- and tetracyclic sulfones with six (n = 1), seven (n = 2) or eight-membered (n = 3) fused-ring systems containing trans-ring junctions unlike the conventional all cis-ring junctions generally obtained during the RRM sequence. Interestingly the starting materials used are simple and commercially available.

ChemInform Abstract: Stereoselective Synthesis of Polycyclic Ring Systems via the Tandem Diels-Alder Reaction.

ChemInform ◽  
2010 ◽  
Vol 26 (23) ◽  
pp. no-no
Author(s):  
J. D. WINKLER ◽  
S. KIM ◽  
K. R. CONDROSKI ◽  
A. ASENSIO ◽  
K. N. HOUK
Keyword(s):  
Stereoselective Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Ring Systems ◽  
Diels Alder Reaction
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