Enantio- and diastereo-selective synthesis of pipecolic acid derivatives using the aza-Diels–Alder reaction of imines with dienes

1991 ◽  
pp. 1337-1340 ◽  
Author(s):  
Patrick D. Bailey ◽  
Robert D. Wilson ◽  
George R. Brown
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Pipecolic Acid ◽  
Selective Synthesis ◽  
Diels Alder Reaction

Highly enantioselective synthesis of pipecolic acid derivatives via an asymmetric aza-Diels–Alder reaction

1994 ◽  
pp. 2543-2544 ◽  
Author(s):  
Patrick D. Bailey ◽  
Derek J. Londesbrough ◽  
Timothy C. Hancox ◽  
John D. Heffernan ◽  
Andrew B. Holmes
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Pipecolic Acid ◽  
Diels Alder Reaction

scholarly journals Thiourea-catalyzed Diels–Alder reaction of a naphthoquinone monoketal dienophile

2013 ◽  
Vol 9 ◽  
pp. 1414-1418 ◽  
Author(s):  
Carsten S Kramer ◽  
Stefan Bräse
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Selective Synthesis ◽  
Quaternary Center ◽  
Diels Alder Reaction ◽  
Cycloaddition Product ◽  
Sterically Hindered ◽  
First Time

A variety of organocatalysts were screened for the catalysis of the naphthoquinone monoketal Diels–Alder reaction. In this study we found that Schreiner's thiourea catalyst 10 and Jacobson's thiourea catalyst 12 facilitate the cycloaddition of the sterically hindered naphthoquinone monoketal dienophile 3 with diene 4. The use of thiourea catalysis allowed for the first time the highly selective synthesis of the exo-product 2a in up to 63% yield. In this reaction a new quaternary center was built. The so formed cycloaddition product 2a represents the ABC tricycle of beticolin 0 (1) and is also a valuable model substrate for the total synthesis of related natural products.

Asymmetric synthesis of pipecolic acid derivatives using the aza-Diels-Alder reaction

1991 ◽  
Vol 2 (12) ◽  
pp. 1263-1282 ◽  
Author(s):  
Patrick D. Bailey ◽  
George R. Brown ◽  
Pritiof Korber ◽  
Amanda Reed ◽  
Robert D. Wilson
Keyword(s):  
Asymmetric Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Pipecolic Acid ◽  
Diels Alder Reaction

Heat Versus Basic Conditions: Intramolecular Dehydro-Diels–Alder Reaction of 1-Indolyl-1,6-heptadiynes for the Selective Synthesis of Substituted Carbazoles

Synlett ◽  
2017 ◽  
Vol 28 (16) ◽  
pp. 2189-2193 ◽  
Author(s):  
Akira Sakakura ◽  
Takayuki Kudoh ◽  
Syo Fujisawa ◽  
Megumi Kitamura
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Selective Synthesis ◽  
Diels Alder Reaction ◽  
High Yields

The intramolecular dehydro-Diels–Alder reaction of 1-indolyl-1,6-heptadiynes proceeds smoothly under rather mild heating conditions to give substituted carbazoles in moderate to good yields. The reaction of 7-aryl-1-indolyl-1,6-heptadiynes under heating gives the corresponding carbazoles chemoselectively in high yields, whereas the reaction under basic conditions gives naphthalenes as major products.

ChemInform Abstract: Highly Enantioselective Synthesis of Pipecolic Acid Derivatives via an Asymmetric Aza-Diels-Alder Reaction.

ChemInform ◽  
2010 ◽  
Vol 26 (17) ◽  
pp. no-no
Author(s):  
P. D. BAILEY ◽  
D. J. LONDESBROUGH ◽  
T. C. HANCOX ◽  
J. D. HEFFERNAN ◽  
A. B. HOLMES
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Enantioselective Synthesis ◽  
Pipecolic Acid ◽  
Diels Alder Reaction

ChemInform Abstract: Asymmetric Synthesis of Pipecolic Acid Derivatives Using the Aza-Diels-Alder Reaction.

ChemInform ◽  
2010 ◽  
Vol 23 (16) ◽  
pp. no-no
Author(s):  
P. D. BAILEY ◽  
G. R. BROWN ◽  
F. KORBER ◽  
A. REED ◽  
R. D. WILSON
Keyword(s):  
Asymmetric Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Pipecolic Acid ◽  
Diels Alder Reaction

The Diels-Alder Reaction of 2-Ethenyl-1,4-Benzodioxin: A New and Simple Synthesis of Bisaryl Ethers

Synlett ◽  
1989 ◽  
Vol 1989 (01) ◽  
pp. 30-32
Author(s):  
Thomas V. Lee ◽  
Alistair J. Leigh ◽  
Christopher B. Chapleo
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Simple Synthesis ◽  
Diels Alder Reaction
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