Silanes in organic synthesis. 9. Enesilylation as a method for 1,2-carbonyl migration within ketones and for conversion to 1,2-transposed allylic alcohols

1980 ◽  
Vol 45 (15) ◽  
pp. 3028-3037 ◽  
Author(s):  
William E. Fristad ◽  
Thomas R. Bailey ◽  
Leo A. Paquette
Keyword(s):  
Organic Synthesis ◽  
Allylic Alcohols

ChemInform Abstract: Tellurium in the “No-Solvent” Organic Synthesis of Allylic Alcohols.

ChemInform ◽  
2010 ◽  
Vol 29 (3) ◽  
pp. no-no
Author(s):  
Q. XU ◽  
B. CHAO ◽  
Y. WANG ◽  
D. C. DITTMER
Keyword(s):  
Organic Synthesis ◽  
Allylic Alcohols

scholarly journals Highly enantioselective isomerization of primary allylic alcohols catalyzed by (P,N)-iridium complexes

2010 ◽  
Vol 82 (7) ◽  
pp. 1461-1469 ◽  
Author(s):  
Luca Mantilli ◽  
David Gérard ◽  
Sonya Torche ◽  
Céline Besnard ◽  
Clément Mazet
Keyword(s):  
Asymmetric Catalysis ◽  
Organic Synthesis ◽  
Industrial Application ◽  
Allylic Alcohols ◽  
Iridium Complexes ◽  
Allylic Amines ◽  
Reaction Conditions ◽  
Significant Challenge ◽  
Catalytic Asymmetric

The catalytic asymmetric isomerization of allylic amines to enamines stands out as one of the most accomplished and well-studied reactions in asymmetric catalysis as illustrated by its industrial application. In contrast, the related asymmetric isomerization of primary allylic alcohols to the corresponding aldehydes still constitutes a significant challenge in organic synthesis. Herein, we show that under appropriate reaction conditions, iridium-hydride catalysts promote the isomerization of primary allylic alcohols under very mild reaction conditions. The best catalysts deliver the desired chiral aldehydes with unprecedented levels of enantioselectivity and good yields. Mechanistic hypotheses have been drawn based on preliminary investigations.

1,3-Oxidative transpositions of allylic alcohols in organic synthesis

Tetrahedron ◽  
2012 ◽  
Vol 68 (27-28) ◽  
pp. 5323-5339 ◽  
Author(s):  
Frederick A. Luzzio
Keyword(s):  
Organic Synthesis ◽  
Allylic Alcohols

Tellurium in the “no-solvent” organic synthesis of allylic alcohols

Tetrahedron ◽  
1997 ◽  
Vol 53 (36) ◽  
pp. 12131-12146 ◽  
Author(s):  
Qinyu Xu ◽  
Bin Chao ◽  
Yongmei Wang ◽  
Donald C. Dittmer
Keyword(s):  
Organic Synthesis ◽  
Allylic Alcohols
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