asymmetric intramolecular olefin aminochlorination using chloride ion†
نویسندگان
چکیده
An iron-catalyzed enantioselective and diastereoselective intramolecular olefin aminochlorination reaction is reported (ee up to 92%, dr up to 15 : 1). In this reaction, a functionalized hydroxylamine and chloride ion are utilized as nitrogen and chlorine sources, respectively. This new method tolerates a range of synthetically valuable internal olefins that are all incompatible with existing asymmetric olefin aminochlorination methods.
منابع مشابه
Iron(II)-catalyzed asymmetric intramolecular olefin aminochlorination using chloride ion†
An iron-catalyzed enantioselective and diastereoselective intramolecular olefin aminochlorination reaction is reported (ee up to 92%, dr up to 15 : 1). In this reaction, a functionalized hydroxylamine and chloride ion are utilized as nitrogen and chlorine sources, respectively. This new method tolerates a range of synthetically valuable internal olefins that are all incompatible with existing a...
متن کاملole fi n aminochlorination using chloride ion †
An iron-catalyzed enantioselective and diastereoselective intramolecular olefin aminochlorination reaction is reported (ee up to 92%, dr up to 15 : 1). In this reaction, a functionalized hydroxylamine and chloride ion are utilized as nitrogen and chlorine sources, respectively. This new method tolerates a range of synthetically valuable internal olefins that are all incompatible with existing a...
متن کاملIntramolecular cycloaddition reactions of silyl nitronate tethered to vinylsilyl group: 2-nitroalkanols as precursors for amino polyols.
[reaction: see text] A method for converting 2-nitroalkanols to precursors for stereodefined amino polyols is described. Diphenylvinylsilylation of the 2-nitroalkanols' hydroxy groups and subsequent silyl nitronate generation by using TMS-Cl and Et(3)N in CH(3)CN at 0 degrees C to room temperature led to fused-bicyclic heterocycles through stereoselective intramolecular nitronate-olefin [3 + 2]...
متن کاملSynthetic studies on bioactive natural polyketides: intramolecular nitrile oxide-olefin cycloaddition approach for construction of a macrolactone skeleton of macrosphelide B.
Studies on the synthesis of macrosphelide B via an intramolecular nitrile oxide-olefin cycloaddition (INOC) is described. In particular, an asymmetric INOC approach using phase transfer catalysts seems to be a potentially efficient and versatile procedure for the construction of the macrolactone skeleton of macrosphelide B in terms of facial selectivity. Our preliminary and unprecedented stereo...
متن کاملCalcium Chloride catalyzed Intramolecular Oxa Michael addition of 2’-Hydroxychalcone to Flavanone
An efficient cyclization of 2’-hydroxychalcone to flavanone using calcium chloride as a catalyst was developed. The scope of the reaction was studied with substituted 2’-hydroxychalcone and these chalcones was converted into corresponding flavanone in good yield. The merits of this method are inexpensive and easily available catalyst, easy workup procedure, avoid use of toxic solvent
متن کامل