scholarly journals DIBALH: from known fundamental to an unusual reaction; chemoselective partial reduction of tertiary amides in the presence of esters

RSC Advances ◽  
2021 ◽  
Vol 11 (53) ◽  
pp. 33809-33813
Author(s):  
Yu Jin Heo ◽  
Hyun Tae Kim ◽  
Ashok Kumar Jaladi ◽  
Duk Keun An

Highly chemoselective partial reduction of tertiary amides to aldehydes over esters are reported with commercial DIBALH. Various aldehydes are synthesized in excellent yields.

2021 ◽  
Vol 50 (7) ◽  
pp. 2354-2358
Author(s):  
Milan Kumar Bisai ◽  
Kritika Gour ◽  
Tamal Das ◽  
Kumar Vanka ◽  
Sakya S. Sen

A very simple and readily accessible lithium compound has been employed to catalyze the hydroboration of tertiary, secondary, and primary amides to the corresponding amines.


2007 ◽  
Vol 179 (7) ◽  
pp. 4919-4928 ◽  
Author(s):  
Daniel J. Powell ◽  
Aloisio Felipe-Silva ◽  
Maria J. Merino ◽  
Mojgan Ahmadzadeh ◽  
Tamika Allen ◽  
...  

1973 ◽  
Vol 51 (13) ◽  
pp. 2102-2104 ◽  
Author(s):  
Donald G. Lee ◽  
James R. Brownridge

The reduction of ethyl phenylpropiolate by lithium aluminum hydride results in partial reduction of the triple bond to give trans-cinnamyl alcohol. If ethyl phenylpropiolate is reduced by LiAlD4 followed by work-up with acetone and H2O the product is the specifically labeled compound, trans-3-phenyl-2-propen-1-ol-1,1,2-d3. If the ester is reduced with LiAlH4 followed by work-up with acetone-d6 and D2O the product is trans-3-phenyl-2-propen-1-ol-O,3-d2. Oxidation of these two products by sodium ruthenate leads to formation of trans-cinnamic acid-α-d and trans-cinnamic acid-β-d, respectively.


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