A Zinc Enolate of Amide: Preparation and Application in Reformatsky-like Reaction Leading to β-Hydroxy Amides

2015 ◽  
Vol 36 (4) ◽  
pp. 1274-1277 ◽  
Author(s):  
Hyun-Hee Cho ◽  
Seung-Hoi Kim
Keyword(s):  
Zinc Enolate

Tandem Chain Extension−Aldol Reaction:  Syn Selectivity with a Zinc Enolate

2001 ◽  
Vol 3 (26) ◽  
pp. 4169-4171 ◽  
Author(s):  
Sujen Lai ◽  
Charles K. Zercher ◽  
Jerry P. Jasinski ◽  
Seth N. Reid ◽  
Richard J. Staples
Keyword(s):  
Aldol Reaction ◽  
Chain Extension ◽  
Zinc Enolate

Conjugate addition approach for natural product synthesis inspired by gibberellin and solanoeclepin A targets

2013 ◽  
Vol 85 (6) ◽  
pp. 1149-1160 ◽  
Author(s):  
Minoru Isobe
Keyword(s):  
Oxygen Atom ◽  
Low Temperatures ◽  
Bond Formation ◽  
Conjugate Addition ◽  
Ring Closure ◽  
Natural Product Synthesis ◽  
Partial Synthesis ◽  
Unsaturated Ketones ◽  
Cyclobutane Ring ◽  
Zinc Enolate

Trimethylzincate is known to react through conjugate addition to α,β-unsaturated ketones, but adds much faster to α,β-unsaturated esters at low temperatures. Since the intermediate zinc enolate behaves differently from that of dimethylcuprate, it offers scope for application in a partial synthesis of gibberellin A3. A second example involving vinylsulfones having an oxygen atom on the γ-carbon strongly directs incoming nucleophiles in conjugate addition mode. Heteroatom-directed conjugate addition (HADCA) provides very reactive carbanion intermediates leading to cyclobutane ring formation, necessary for synthesis of solanoeclepin A. An alternative reaction for the four-membered carbocyclic ring closure was explored to make a bond formation between the propargylic cation of Nicholas type and allyltrimethylsilane nucleophile of Hosomi–Sakurai type. This method allowed a formation of tricyclo[5.2.1.01,6]decene framework.

One-pot reactions of bicyclic zinc enolate generated from Ni-catalyzed reductive cyclization to furnish octahydro-4,7-ethanobenzofuran-9-one derivatives

2019 ◽  
Vol 60 (42) ◽  
pp. 151148
Author(s):  
Tetsuya Tsujihara ◽  
Moriho Tomeba ◽  
Shigeaki Ohkubo-Sato ◽  
Kyoko Iwabuchi ◽  
Rino Koie ◽  
...  
Keyword(s):  
Reductive Cyclization ◽  
One Pot ◽  
Zinc Enolate

ChemInform Abstract: Reaction of Thionolactones with Zinc Enolate: New Synthesis of Vinylogous Carbonates.

ChemInform ◽  
2010 ◽  
Vol 30 (45) ◽  
pp. no-no
Author(s):  
Hyeon Kyu Lee ◽  
Jia Kim ◽  
Chwang Siek Pak
Keyword(s):  
New Synthesis ◽  
Zinc Enolate
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