130693-83-3Relevant articles and documents
Reagent-controlled stereoselectivity in titanocene-catalyzed epoxide openings: Reductions and intermolecular additions to α,β-unsaturated carbonyl compounds
Gansaeuer, Andreas,Bluhm, Harald,Rinker, Bjoern,Narayan, Sanjay,Schick, Michael,Lauterbach, Thorsten,Pierobon, Marianna
, p. 531 - 542 (2003)
The generation and addition reactions of metal bound radicals derived from normal and meso epoxides by electron transfer from titanocene(III) reagents is described. The control of enantioselectivity and diastereoselectivity of these transformations is inv
Stereoselective synthesis of constrained norbornane-derived spiro-β-lactams
Cremonesi, Giuseppe,Dalla Croce, Piero,Forni, Alessandra,La Rosa, Concetta
, p. 1175 - 1182 (2013/03/13)
New enantiopure polycyclic norbornane-derived spiro-β-lactams were synthesized by means of a Staudinger ketene-imine reaction between unsymmetrical bicyclic chiral ketenes, generated from differently substituted norbornane carboxylic acids, and (E)-N-benzyl-N-(phenylmethylene)amine, with high yields and moderate to good stereoselectivities. The diastereoisomeric results were rationalized taking into account the increasing steric encumbrance present on the norbornane skeleton and the stability of the products. The configurations of the newly formed stereocenters of spiro-β-lactams were assigned on the basis of 2D NMR experiments and X-ray analysis. Spiro-β-lactams were subjected to acid hydrolysis obtaining the corresponding norbornane-derived β-amino acids.
Alkylmetal Asymmetric Reduction. 18. Starting Materials in the Preparation of New Chiral Reducing Agents: Synthetic Approach to Primary Alkyl Halides Derived from (+)-Camphor
Falorni, Massimo,Lardicci, Luciano,Giacomelli, Giampaolo
, p. 5291 - 5294 (2007/10/02)
2,2-Dimethyl-3-(chloromethyl)bicycloheptane (camphanyl chloride), camphanyl bromide, 1,7,7-trimethyl-2-(chloromethyl)bicycloheptane , and 2-(bromomethyl)bornane were prepared from (+)-camphor.All these compounds were obtained as mixture of exo and endo isomers in various ratios depending upon the synthetic path adopted.A loss of diastereomeric purity during the halogenations of corresponding alcohols was observed.