674309-47-8Relevant academic research and scientific papers
Synthesis of stereodefined substituted cycloalkenes by a one-pot catalytic boronation-allylation-metathesis sequence
Selander, Nicklas,Szabo, Kalman J.
experimental part, p. 2045 - 2051 (2009/08/10)
Stereodefined cyclohexene and cyclopentene derivatives were prepared bythe coupling of allylic alcohols and other allylic precursors with unsaturated aldehydes. These reactions are based on a multicatalytic one-pot approach involving palladium pincer complex-catalyzed boronation, allylation and ring-closing metathesis reactions. This reaction sequence can be performed in an operationally simple procedure affording the cycloalkene products in high overall yields and excellent regio- and stereoselectivities. The presented procedure has a broad synthetic scope and high functional group tolerance, which allows the synthesis of bicyclic lactone and spirane skeletons and various substitution patterns including hydroxy, silyl, vinyl, allyl, and sulfonyl groups. The studied catalytic one-pot reactions involve up to three individual processes performed by up to four acid-and transition metal-catalyzed events.
Enantioselective preparation of a novel chiral 1,2-diamine
Demay, Stéphane,Kotschy, Andras,Knochel, Paul
, p. 863 - 866 (2007/10/03)
A short enantioselective preparation of (1S,2S)-trans-1,2-diamino-3-cyclohexene using a double [3,3]-sigmatropic rearrangement of an allylic bis(imidate) is described (Overman rearrangement). The starting chiral diol is conveniently obtained by enzymatic resolution.
New C2-symmetrical 1,2-diphosphanes for the efficient rhodium-catalyzed asymmetric hydroboration of styrene derivatives
Demay, Steandphane,Volant, Florence,Knochel, Paul
, p. 1235 - 1238 (2007/10/03)
A double [2,3] sigmatropic rearrangement enables the fast synthesis of novel C2-symmetrical 1,2-diphosphanes in good yields. These phosphanes (for example, 1; c-Hex = cyclohexyl) are highly efficient ligands for the rhodium-catalyzed asymmetric hydroboration of a wide variety of styrenes (see scheme). cod = 1,5-cyclooctadiene; DME = 1,2-dimethoxyethane.
