Organic Chemistry Portal
Reactions > Organic Synthesis Search

Categories: C-N Bond Formation > Amines > Synthesis of primary amines >

Synthesis of protected primary amines

Related:
carbamates

sulfonamides


Recent Literature


A new, simple method for the conversion of alcohols to tosylamides is presented.
M. C. Marcotullio, V. Campagna, S. Sternativo, F. Costantino, M. Curini, Synthesis, 2006, 2760-2766.


A three-component condensation of aldehydes, benzyl carbamate and allyltrimethylsilane, which affords corresponding protected homoallylic amines in excellent yields, is catalyzed by iodine.
P. Phukan, J. Org. Chem., 2004, 69, 4005-4006.


An efficient palladium-catalyzed asymmetric amination of 2,3-allenyl phosphates with nitrogen nucleophiles such as amines, hydroxylamines, and imides can be performed in presence of SEGPHOS or MeOBIPHEP ligand, affording the corresponding optically active 1-aminated derivatives with high enantiomeric excess.
Y. Imada, M. Nishida, K. Kutsuwa, S.-I. Murahashi, T. Naota, Org. Lett., 2005, 7, 5837-5839.


A mild, gold(I)-catalyzed hydroamination of 1,3-dienes is reported. Various carbamates and sulfonamides add to conjugated dienes to affort protected allylic amines in good to high yields.
C. Brouwer, C. He, Angew. Chem. Int. Ed., 2006, 45, 1744-1747.


Ph3PAuOTf catalyzes efficient intra- and intermolecular hydroamination of unactivated olefins with sulfonamides.
J. Zhang, C.-G. Yang, C. He, J. Am. Chem. Soc., 2006, 128, 1798-1799.


Copper(II) trifluoromethanesulfonate catalyzed a mild amidation of cyclic ethers with iminoiodanes with good yields and selectivity. A subsequent reductive ring-opening of the tosylamidated products gives α,ϖ-amino alcohols.
L. He, J. Yu, J. Zhang, X.-Q. Yu, Org. Lett., 2007, 9, 2277-2280.


An efficient amidation reaction of saturated C-H bonds catalyzed by a unique disilver(I) complex is reported. The reaction is stereospecific and practical for the construction of amine-containing molecules.
Y. Cui, C. He, Angew. Chem. Int. Ed., 2004, 43, 4210-4212.


Y. Cui, C. He, Angew. Chem. Int. Ed., 2004, 43, 4210-4212.


A new procedure for aminobromination of olefins gives vicinal bromoamine derivatives in high yields using Cu, Mn, or V catalysts with p-toluenesulfonamide as nitrogen source and N-bromosuccinimide (NBS) as bromine source. Excellent regio- and stereoselectivity is shown for different olefinic substrates as well as transition metal catalysts.
V. V. Thakur, S. K. Talluri, A. Sudalai, Org. Lett., 2003, 5, 861-864.

Related:


An efficient dynamic kinetic resolution of amines combines a ruthenium-catalyzed racemization with a lipase-catalyzed resolution. A variety of primary amines were transformed into one enantiomer of the amide in high yield and high enantioselectivity.
J. Paetzold, J. E. Bäckvall, J. Am. Chem. Soc., 2005, 127, 17620-17621.


A practical procedure for an efficient dynamic kinetic resolution of primary amines employs a palladium nanocatalyst as racemization catalyst, a commercial lipase as resolution catalyst, and ethyl acetate or ethyl methoxyacetate as acyl donor. Various amines and one amino acid amide have been resolved with good yields and high enantiomeric excesses.
M.-J. Kim, W.-H. Kim, K. Han, Y. K. Choi, J. Park, Org. Lett., 2007, 9, 1157-1159.


M.-J. Kim, W.-H. Kim, K. Han, Y. K. Choi, J. Park, Org. Lett., 2007, 9, 1157-1159.