192655-86-0Relevant academic research and scientific papers
Synthesis of bicyclic cyclopropylamines from amino acid derivatives
Faler, Catherine A.,Cao, Bin,Joullie, Madeleine M.
, p. 519 - 522 (2007/10/03)
The synthesis of novel [3.1.0] bicyclic cyclopropylamines from differently substituted amino acids using Ti(II)-mediated coupling and the extension of this methodology to provide [4.1.0] systems is described.
3-azabicyclo[3.1.0]hex-1-ylamines by Ti-mediated intramolecular reductive cyclopropanation of α-(N-allylamino)-substituted N,N-dialkylcarboxamides and carbonitriles
Gensini, Martina,Kozhushkov, Sergei I.,Yufit, Dmitrii S.,Howard, Judith A. K.,Es-Sayed, Mazen,De Meijere, Armin
, p. 2499 - 2507 (2007/10/03)
A variety of tris- and monoprotected derivatives with the 1-amino-3-azabicyclo[3.1.0]hexane and 1-amino-3-azabicy- clo[4.1.0]heptane skeleton 10 have been synthesized by intramolecular reductive cyclopropanation of α-(N-allylamino)-substituted N,N-dialkylcarboxamides 6, 8, and 9. Starting from derivatives of the naturally occurring amino acid serine (4a, 4b), the enantiomerically pure compounds 10a and 10b were obtained with endo/exo ratios of 2.5:1 (a) and 2:1 (b), in 26 and 30% overall yields, respectively. The unprotected bicyclic amines 11aa, 11ab, 11ba, and 11ad have been prepared by palladium-catalyzed hydrogenative deprotection of 10aa, 10ab, 10ba and 10ad, respectively, under acidic conditions, in 91, 95, 96, and 99% yields, respectively. X-ray crystal structure analyses of 10aa and 10ad in each case found an equatorial position of the N-benzyl group on the heterocycle and a common boat conformation for the 3-azabicyclo[3.1.0]hexane and 3-azabicyclo[4.1.0]heptane skeletons as a whole. One-step preparations of the bicyclic diamiries 11ac (41% yield) and 14a (48% yield) have been performed by application of the Kulinkovich-de Meijere procedure to the nitriles 12a and 12b. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
