Synthetic applications of glycidic thiolesters. Regioselective reduction to 1,3-diols and 2,3-epoxy alcohols

1992 ◽  
Vol 70 (1) ◽  
pp. 128-134 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Weide Luo
Keyword(s):  
Raney Nickel ◽  
Sodium Borohydride ◽  
Room Temperature ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Epoxy Alcohols

Glycidic thiolesters were shown to undergo regioselective reduction with Raney nickel to give 1,3-diols. With sodium borohydride at room temperature and lithium aluminum hydride at −78 °C, the reduction of glycidic thiolesters was found to proceed chemoselectively to furnish 2,3-epoxy alcohols. Keywords: glycidic thiolesters, reduction, 1,3-diols, 2,3-epoxy alcohols.

THE REACTION OF DIETHYL AZODICARBOXYLATE WITH DIHYDROGELSEMINE

1955 ◽  
Vol 33 (4) ◽  
pp. 604-609 ◽  
Author(s):  
Thelma Habgood ◽  
Léo Marion
Keyword(s):  
Infrared Spectrum ◽  
Methyl Ether ◽  
Sodium Borohydride ◽  
Lithium Aluminum Hydride ◽  
Chromic Acid ◽  
Aluminum Hydride ◽  
Membered Ring ◽  
Lithium Aluminum ◽  
Diethyl Azodicarboxylate ◽  
Methylene Group

Dihydrogelsemine reacts with diethyl azodicarboxylate yielding a carbinolamine which forms a methyl ether. Both this ether and the carbinolamine base can be oxidized by chromic acid to the same neutral lactam. That there has been no rearrangement of the carbon skeleton during these reactions is shown by reduction of the methyl ether of the carbinolamine with sodium borohydride to dihydrogelsemine and by reduction of the lactam with lithium aluminum hydride to tetrahydrodesoxygelsemine. It is concluded that both dihydrogelsemine and gelsemine contain a methylene group adjacent to N(b), and from the infrared spectrum of the lactam of dihydrogelsemine, N(b) appears to be part of a five-membered ring.

Non-catalytic conversion of C–F bonds of gem-difluoromethylene derivatives to C–H bonds with lithium aluminum hydride under room temperature

Tetrahedron ◽  
2011 ◽  
Vol 67 (2) ◽  
pp. 285-288 ◽  
Author(s):  
Jing-Jing Wu ◽  
Jian-Hang Cheng ◽  
Jian Zhang ◽  
Li Shen ◽  
Xu-Hong Qian ◽  
...  
Keyword(s):  
Room Temperature ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Catalytic Conversion ◽  
Lithium Aluminum
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