60416-25-3Relevant articles and documents
Regioselective rhodium-catalyzed hydroformylation of 1,3-dienes to highly enantioenriched β,γ-unsaturated aldehyes with diazaphospholane ligands
Watkins, Avery L.,Landis, Clark R.
supporting information; scheme or table, p. 164 - 167 (2011/04/12)
Regioselective and enantioselective rhodium-catalyzed hydroformylation of 1,3-dienes with chiral bisdiazaphospholane ligands yields β,γ- unsaturated aldehydes that retain a C=C functionality for further conversion. The reaction conditions are mild, featuring low catalyst loadings (0.5 mol %), pressures readily obtained in glass bottles, and convenient reaction times (1.5-12 h). Optimized reaction conditions produce high enantioselectivity (>90% ee), regioselectivity (88-99%), and conversion to β,γ- unsaturated aldehydes (99%) for ten 1,3-dienes encompassing a variety of substitution patterns.
Studies concerning the electrophilic amino-alkene cyclisation for the synthesis of bicyclic amines
Klein, Johannes E. M. N.,Mueller-Bunz, Helge,Evans, Paul
supporting information; experimental part, p. 986 - 995 (2009/05/30)
The bromination of a series of cyclohexenyl substituted secondary amines 1a-i has been investigated using Br2, PHT and NBS. In the case of Br2 and NBS the secondary amines preferentially undergo N-bromination. In contrast, PHT cleanly affords the products of alkene dibromination. In the case of Br2 the N-bromo species then give the products of alkene dibromination, albeit less efficiently. On subsequent treatment with K2CO3 these dibromides form the corresponding hexahydroindoles 2a-h and octahydroquinoline 2i. The presence of an N-substituent bearing a stereogenic centre (1h and 1i) was studied and the products 2h and 2i were isolated with no diastereoselectivity. When NBS was used a novel cyclisation, forming bromo-substituted octahydroindoles 9a,b and d, was observed. In relation to this sequence it was shown that these products were not intermediates in the former Br2/PHT processes and that the reaction only proceeded in the presence of the succinimide by-product of N-bromination.
γ,δ- and δ,ε-unsaturated aldehydes from γ- and δ-lactones in one step: Preliminary communication
Giersch, Wolfgang,Naef, Ferdinand
, p. 1697 - 1703 (2007/10/03)
A one-step transformation of δ- and δ-(spiro)lactones into δ,δ- and δ,ε-unsaturated aldehydes with an excess of formic acid in the vapor phase over a supported manganese catalyst is described for the first time. The scope and limitations of this new reaction are shown with different lactones as substrate, and a mechanistic rationale is proposed.
