Stereo-controlled synthesis of polyheterocycles via the diene-transmissive hetero-Diels–Alder reaction of β,γ-unsaturated α-keto esters

2015 ◽  
Vol 13 (21) ◽  
pp. 5875-5879 ◽  
Author(s):  
Takashi Otani ◽  
Yumiko Tamai ◽  
Kazunori Seki ◽  
Tomohiro Kikuchi ◽  
Taiichiro Miyazawa ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Controlled Synthesis ◽  
Keto Esters ◽  
Diels Alder Reaction ◽  
Stereocontrolled Synthesis

Stereocontrolled synthesis of polyheterocycles via the diene-transmissive hetero Diels–Alder reaction of β,χ-unsaturated α-keto esters is described.

ChemInform Abstract: Stereo-Controlled Synthesis of Polyheterocycles via the Diene-Transmissive hetero-Diels-Alder Reaction of β,γ-Unsaturated α-Keto Esters.

ChemInform ◽  
2015 ◽  
Vol 46 (39) ◽  
pp. no-no
Author(s):  
Takashi Otani ◽  
Yumiko Tamai ◽  
Kazunori Seki ◽  
Tomohiro Kikuchi ◽  
Taiichiro Miyazawa ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Controlled Synthesis ◽  
Keto Esters ◽  
Diels Alder Reaction

First hetero-diels-alder reaction of an enantiopure 2-sulfinylbuta-1, 3-diene: mild and effective stereocontrolled synthesis of pyranoid derivatives

1997 ◽  
Vol 8 (17) ◽  
pp. 2989-2995 ◽  
Author(s):  
Maria C. Aversa ◽  
Anna Barattucci ◽  
Paola Bonaccorsi ◽  
Giuseppe Bruno ◽  
Placido Giannetto ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Stereocontrolled Synthesis

Direct construction of chiral quaternary dihydropyranones through highly enantioselective organocatalytic hetero-Diels–Alder reactions of olefinic azlactones

2016 ◽  
Vol 3 (5) ◽  
pp. 598-602 ◽  
Author(s):  
Tai-Ping Gao ◽  
Dan Liu ◽  
Jun-Bing Lin ◽  
Xiu-Qin Hu ◽  
Zhu-Yin Wang ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Direct Construction ◽  
Keto Esters ◽  
Diels Alder Reaction

The first organocatalytic hetero-Diels–Alder reaction of an in situ generated diene with α-keto esters was reported for the construction of chiral dihydropyranones.

Stereocontrolled construction of 1,7-dimethyl A.B.C.[6.6.6] tricycles. Part I. Transannular Diels–Alder reactions of 14-membered macrocycles containing trans-dienophiles

1993 ◽  
Vol 71 (8) ◽  
pp. 1152-1168 ◽  
Author(s):  
Yao-Chang Xu ◽  
Andrew L. Roughton ◽  
Raymond Plante ◽  
Solo Goldstein ◽  
Pierre Deslongchamps
Keyword(s):  
Natural Products ◽  
Alder Reaction ◽  
Diels Alder ◽  
Methyl Substituent ◽  
Dimethyl Malonate ◽  
General Methodology ◽  
Racemic Form ◽  
Diels Alder Reaction ◽  
Tricyclic Compounds ◽  
Stereocontrolled Synthesis

Transannular Diels–Alder reactions of 14-membered macrocyclic trienes possessing a methyl substituent on both the diene and dienophile moiety have been investigated. Macrocyclic structures 1a, 1b, and 1c having cis-trans-trans (CTT), trans-cis-trans (TCT), and trans-trans-trans (TTT) geometries could be stereoselectively constructed by coupling appropriately functionalized dienes 5 and dienophile 4 following an intramolecular displacement of an allylic halide by the anion of an appropriately located dimethyl malonate unit. The transannular Diels–Alder reaction performed on 1a led to a mixture of four major tricyclic products, including 34 possessing the unexpected trans-anti-cis (TAC) stereochemistry. When heated at 300 °C, macrocycle 1b underwent an unique conversion via an ene–retroene, Diels–Alder process, producing the unexpected tricycle 41 (racemic form) containing five contiguous chiral centers. A rationale for the above experimental facts is presented. In contrast to the previous results, the transannular Diels–Alder reaction of macrocycle 1c was straightforward, producing a 95% isolated yield of trans-anti-cis (TAC) tricycle 34. This investigation demonstrates a general methodology for the stereocontrolled synthesis of 1,2-dimethyl A.B.C[6.6.6] tricyclic compounds, which are potential precursors to polycyclic natural products such as steroids and terpenes.

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