Synthesis of 2-allyl-2,3-dihydro-1H-indol-3-ones using in situ Claisen rearrangement of 2,3-dihydro-1H-indol-3-ones with allyl alcohols

1996 ◽  
pp. 729 ◽  
Author(s):  
Tomomi Kawasaki ◽  
Kouhei Masuda ◽  
Yasutaka Baba ◽  
Romi Terashima ◽  
Kana Takada ◽  
...  
Keyword(s):  
Claisen Rearrangement ◽  
Allyl Alcohols

ChemInform Abstract: Synthesis of 1,2-Dihydro-2-allylindol-3-ones Using in situ Claisen Rearrangement of 1,2-Dihydroindol-3-ones with Allyl Alcohols

ChemInform ◽  
2010 ◽  
Vol 26 (18) ◽  
pp. no-no
Author(s):  
T. KAWASAKI ◽  
K. MASUDA ◽  
Y. BABA ◽  
K. TAKADA ◽  
M. SAKAMOTO
Keyword(s):  
Claisen Rearrangement ◽  
Allyl Alcohols

ChemInform Abstract: Synthesis of 2-Allyl-2,3-dihydro-1H-indol-3-ones Using in situ Claisen Rearrangement of 2,3-Dihydro-1H-indol-3-ones with Allyl Alcohols.

ChemInform ◽  
2010 ◽  
Vol 27 (30) ◽  
pp. no-no
Author(s):  
T. KAWASAKI ◽  
K. MASUDA ◽  
Y. BABA ◽  
R. TERASHIMA ◽  
K. TAKADA ◽  
...  
Keyword(s):  
Claisen Rearrangement ◽  
Allyl Alcohols

scholarly journals Synthesis of 1,2-Dihydro-2-allylindol-3-ones Using in Situ Claisen Rearrengement of 1,2-Dihydroindol-3-ones with Allyl Alcohols.

1994 ◽  
Vol 42 (9) ◽  
pp. 1974-1976 ◽  
Author(s):  
Tomomi KAWASAKI ◽  
Kouhei MASUDA ◽  
Yasutaka BABA ◽  
Kana TAKADA ◽  
Masanori SAKAMOTO
Keyword(s):  
Allyl Alcohols

Asymmetric Synthesis of a Hydroxylated Nine-membered Lactone from Tartaric Acid using the Claisen Rearrangement

2010 ◽  
Vol 63 (3) ◽  
pp. 529 ◽  
Author(s):  
Leon S.-M. Wong ◽  
Kathleen A. Turner ◽  
Jonathan M. White ◽  
Andrew B. Holmes ◽  
John H. Ryan
Keyword(s):  
Natural Products ◽  
Asymmetric Synthesis ◽  
Tartaric Acid ◽  
Claisen Rearrangement ◽  
Cyclic Carbonate ◽  
Thermal Elimination ◽  
Ketene Acetal ◽  
Medium Ring

The synthesis of a hydroxylated vinyl-appended lactone, in five synthetic steps from tartaric acid, is reported. The C2-symmetrical bis-vinyl diol 12 was converted into the ketene acetal 14 via methylenation of the cyclic carbonate 13 or thermal elimination of benzeneselenenic acid from the selenoxide 17. In both cases, the in situ generated ketene acetal 14 underwent spontaneous Claisen rearrangement to give the nine-membered lactone (+)-15. Lactones of this type are potentially advanced precursors to simplified eleutherobin analogues or other medium-ring lactone natural products.

Stereoselective Synthesis of (Z)-Allyl Alcohols through Coinage-Metal-Catalyzed Nucleophilic Addition of Benzo[d]isoxazoles with Unactivated Propargyl Alcohols

Synlett ◽  
2019 ◽  
Vol 30 (11) ◽  
pp. 1339-1345
Author(s):  
Zhiyuan Chen ◽  
Wenjin Wu ◽  
Tiantian Zheng ◽  
Jie Tan ◽  
Shouzhi Pu
Keyword(s):  
Stereoselective Synthesis ◽  
Silver Salt ◽  
Gold Catalyst ◽  
Building Blocks ◽  
Coinage Metal ◽  
Stereoselective Addition ◽  
Allyl Alcohols ◽  
Metal Catalyzed ◽  
Propargyl Alcohols

The Au/Ag-cocatalyzed stereoselective addition reaction of cyanophenol anion species generated in situ with unactivated propargyl alcohols to produce functionalized (Z)-allyl alcohols in mostly good yields is reported. Benzo[d]isoxazoles were found to be excellent building blocks for the production of highly reactive cyanophenol anions from Kemp elimination reactions, thus serving as a masked benzonitrile source for the preparation of organonitrile derivatives. Silver salt combined with gold catalyst were found to be necessary for the success of this transformation.

scholarly journals Direct C–H Alpha Arylation of Enones with ArI(O2CR)2 Reagents

2019 ◽  
Author(s):  
Felipe Cesar Sousa e Silva ◽  
Nguyen T Van ◽  
Sarah Wengryniuk
Keyword(s):  
Claisen Rearrangement ◽  
Bond Formation ◽  
Hypervalent Iodine ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Metal Free ◽  
Wide Range ◽  
Reaction Proceeds ◽  
Mechanistic Investigations

Herein, we report the metal-free direct C–H arylation of enones mediated by hypervalent iodine reagents. The reaction proceeds via a reductive iodonium Claisen rearrangement of <i>in situ </i>b-pyridinium silyl enol ethers. The aryl groups are derived from ArI(O<sub>2</sub>CCF<sub>3</sub>)<sub>2</sub> reagents, which are readily accessed from the parent iodoarenes. It is tolerant of a wide range of substitution patterns and the incorporated arenes maintain the valuable iodine functional handle. Mechanistic investigations implicate arylation via an umpoled “enolonium” species and that the presence of a b-pyridinium moiety is critical for desired C–C bond formation.

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