Regiospecific synthesis of .beta.,.gamma.-unsaturated ketones from allylic alcohols. Claisen rearrangement of .alpha.-allyloxy ketone enol derivatives

1986 ◽  
Vol 51 (9) ◽  
pp. 1393-1401 ◽  
Author(s):  
Joseph L. C. Kachinsky ◽  
Robert G. Salomon
Keyword(s):  
Claisen Rearrangement ◽  
Allylic Alcohols ◽  
Unsaturated Ketones

Syntheses of trifluoromethylated diene derivatives through the claisen rearrangement of trifluoromethylated propargylic and allylic alcohols

1985 ◽  
Vol 26 (2) ◽  
pp. 219-222 ◽  
Author(s):  
Yuji Hanzawa ◽  
Kei-ichi Kawagoe ◽  
Akio Yamada ◽  
Yoshiro Kobayashi
Keyword(s):  
Claisen Rearrangement ◽  
Allylic Alcohols

Iridium-catalyzed regioselective decarboxylative allylation of β-ketoacids: efficient construction of γ,δ-unsaturated ketones

2015 ◽  
Vol 51 (57) ◽  
pp. 11512-11514 ◽  
Author(s):  
Shu-Jie Chen ◽  
Guo-Ping Lu ◽  
Chun Cai
Keyword(s):  
Allylic Alcohols ◽  
Unsaturated Ketones ◽  
Efficient Construction ◽  
Decarboxylative Allylation

A highly regioselective protocol is reported for the efficient construction of γ,δ-unsaturated ketones from β-ketoacids and allylic alcohols.

Chemoselective Reduction of Complexα,β-Unsaturated Ketones to Allylic Alcohols over Ir-Metal Particles onβ Zeolites

2003 ◽  
Vol 42 (43) ◽  
pp. 5333-5336 ◽  
Author(s):  
Mario De bruyn ◽  
Simona Coman ◽  
Roxana Bota ◽  
Vasile I. Parvulescu ◽  
Dirk E. De Vos ◽  
...  
Keyword(s):  
Metal Particles ◽  
Allylic Alcohols ◽  
Unsaturated Ketones

Sequential O-Arylation/Lanthanide(III)-Catalyzed [3,3]-Sigmatropic Rearrangement of Bromo-Substituted Allylic Alcohols

Synlett ◽  
2017 ◽  
Vol 28 (20) ◽  
pp. 2865-2870 ◽  
Author(s):  
Timothy Ramadhar ◽  
Jun-ichi Kawakami ◽  
Robert Batey
Keyword(s):  
Claisen Rearrangement ◽  
Cross Coupling ◽  
Sigmatropic Rearrangement ◽  
Mitsunobu Reaction ◽  
Allylic Alcohols ◽  
Aryl Ether ◽  
Claisen Rearrangements ◽  
Snar Reaction ◽  
Aryl Ethers

Lanthanide(III)-catalyzed aryl-Claisen rearrangement of substrates bearing halo-substituted allyl groups, specifically 2-bromoallyl aryl ethers, afford ortho-2-bromoallylphenols. Aryl ether substrates were synthesized from brominated allylic alcohols via Mitsunobu reaction, Cu(II)-catalyzed arylation using potassium aryltrifluoroborate salts, or SNAr reaction. Aryl-Claisen rearrangements proceeded in moderate to excellent yields using Eu(III) catalysis. The alkenylbromide functionality remains intact, illustrating the compatibility of synthetically important alkenylhalides during C–O/C–C σ-bond migration processes. Subsequent derivatization of the ortho-2-bromoallylphenol products through O-alkylation or C-arylation/alkenylation via Suzuki–Miyaura cross-coupling demonstrate the potential to access densely-functionalized molecules.

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