Diisobutylaluminum borohydride: An efficient reagent for the reduction of tertiary amides to the corresponding amines under ambient conditions

Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups

“…A preliminary work demonstrated that this binary hydride reduced tertiary amides to amines at 25 °C. 12 Thus, it was decided to examine the reducing characteristics of (iBu) 2 AlBH 4 toward representative organic functional groups at 25 °C. Herein, we report the scope and limitations of (iBu) 2 AlBH 4 as a reducing agent.…”

Unraveling the C2-Symmetric Azatetraquinane System. Simple, Enantioselective Syntheses

“…Ketone 20 was converted via the vinyl triflate 21 to the α,β-unsaturated nitrile 22 , which was then reduced to the amino nitrile 23 , hydrolysis of which gave the amino acid 24 . The synthesis of (±)- 1 by this route was completed by lactamization to 25 and two-stage reduction . This route also provides access to chiral 1 and ent - 1 starting with chiral nitrone 8 .…”

“…The synthesis of (±)-1 by this route was completed by lactamization to 25 16 and two-stage reduction. 17 This route also provides access to chiral 1 and ent-1 starting with chiral nitrone 8.…”

Facile titanium(IV) chloride and TBD‐mediated synthesis of N‐aryl‐substituted azacycles from arylhydrazines

“…1 Moreover, N-substituted heterocycle structures such as N-substituted azacycles are observed commonly in various natural compounds with biologically active properties 2 and in several FDA-approved drugs. 3 Due to the meaningful contribution of N-substituted heterocycles to human life, a variety of synthetic procedures to generate N-substituted azacycles have been developed: amination of dihalides or diols by arylamines, 4 crosscoupling reactions for the formation of C N linkages from aryl halides, 5 reductive amination, 6 reduction of tertiary amides, 7 reduction of tertiary lactams, 8 hydrogenation of N-heteroaromatics, 9 intramolecular C(sp 3 )-N coupling reactions, 10 intramolecular C(sp 3 )-N amination, 11 Mitsunobu cyclodehydration reactions for preparation of bicyclic and cyclic N-arylamines, 12 and the Prins cyclization reaction. 13 Additionally, several reactions of primary arylamines with cyclic ethers to yield azacycles have been reported due to their release of environmental byproducts such as water during the reactions.…”

“…Due to the meaningful contribution of N ‐substituted heterocycles to human life, a variety of synthetic procedures to generate N ‐substituted azacycles have been developed: amination of dihalides or diols by arylamines, 4 cross‐coupling reactions for the formation of CN linkages from aryl halides, 5 reductive amination, 6 reduction of tertiary amides, 7 reduction of tertiary lactams, 8 hydrogenation of N ‐heteroaromatics, 9 intramolecular C(sp 3 )‐N coupling reactions, 10 intramolecular C(sp 3 )‐N amination, 11 Mitsunobu cyclodehydration reactions for preparation of bicyclic and cyclic N ‐arylamines, 12 and the Prins cyclization reaction 13 …”