Allylation of 2-Azaallyls with Allyl Ethers

Synfacts ◽  
2021 ◽  
Vol 17 (09) ◽  
pp. 1004
Keyword(s):  
Allyl Ethers

scholarly journals Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Guogang Deng ◽  
Shengzu Duan ◽  
Jing Wang ◽  
Zhuo Chen ◽  
Tongqi Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Allyl Ether ◽  
Metal Catalyst ◽  
Metal Free ◽  
Allyl Ethers ◽  
Bond Forming ◽  
Allyl Halides ◽  
Synthetic Utility ◽  
Insight Into ◽  
Allyl Esters

AbstractAllylation of nucleophiles with highly reactive electrophiles like allyl halides can be conducted without metal catalysts. Less reactive electrophiles, such as allyl esters and carbonates, usually require a transition metal catalyst to facilitate the allylation. Herein, we report a unique transition-metal-free allylation strategy with allyl ether electrophiles. Reaction of a host of allyl ethers with 2-azaallyl anions delivers valuable homoallylic amine derivatives (up to 92%), which are significant in the pharmaceutical industry. Interestingly, no deprotonative isomerization or cyclization of the products were observed. The potential synthetic utility and ease of operation is demonstrated by a gram scale telescoped preparation of a homoallylic amine. In addition, mechanistic studies provide insight into these C(sp3)–C(sp3) bond-forming reactions.

scholarly journals Synthesis of 5,6,7,8-Tetrahydroquinolines by Thermolysis of Oxime O-Allyl Ethers in the Presence of Boron Trifluoride Etherate.

1993 ◽  
Vol 41 (7) ◽  
pp. 1297-1298 ◽  
Author(s):  
Junko KOYAMA ◽  
Tamaki OGURA ◽  
Kiyoshi TAGAHARA ◽  
Masaaki MIYASHITA ◽  
Hiroshi IRIE
Keyword(s):  
Boron Trifluoride ◽  
Boron Trifluoride Etherate ◽  
Allyl Ethers

Regioselective hydroformylation of cyclic vinyl and allyl ethers with rhodium catalysts. Crucial influence of the size of the phosphorus cocatalyst

1992 ◽  
Vol 11 (11) ◽  
pp. 3525-3533 ◽  
Author(s):  
Alfonso Polo ◽  
Carmen Claver ◽  
Sergio Castillon ◽  
Aurora Ruiz ◽  
Juan Carlos Bayon ◽  
...  
Keyword(s):  
Rhodium Catalysts ◽  
Allyl Ethers

Gas phase thermolysis of alkyl allyl ethers, thioethers and amines

1989 ◽  
Vol 38 (1) ◽  
pp. 153-158 ◽  
Author(s):  
G. Martin ◽  
J. Ascanio
Keyword(s):  
Gas Phase ◽  
Allyl Ethers

ChemInform Abstract: Enantioselective Claisen Rearrangement of Difluorovinyl Allyl Ethers.

ChemInform ◽  
2010 ◽  
Vol 30 (10) ◽  
pp. no-no
Author(s):  
Hisanaka Ito ◽  
Azusa Sato ◽  
Tetsuo Kobayashi ◽  
Takeo Taguchi
Keyword(s):  
Claisen Rearrangement ◽  
Allyl Ethers

ChemInform Abstract: (2,3) VS (3,3), THE NOVEL (2,3)SIGMATROPIC REARRANGEMENT OF OXIME-O-ALLYL ETHERS

1973 ◽  
Vol 4 (52) ◽  
pp. no-no
Author(s):  
S. RANGANATHAN ◽  
D. RANGANATHAN ◽  
R. S. SIDHU ◽  
A. K. MEHROTRA
Keyword(s):  
Sigmatropic Rearrangement ◽  
The Novel ◽  
Allyl Ethers

Synthesis of Enantioenriched Secondary and Tertiary Alcohols via Tricarbonylchromium(0) Complexes of Benzyl Allyl Ethers

2009 ◽  
Vol 2009 (10) ◽  
pp. 1606-1611 ◽  
Author(s):  
Keren Abecassis ◽  
Susan E. Gibson ◽  
Mar Martin-Fontecha
Keyword(s):  
Allyl Ethers ◽  
Tertiary Alcohols
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