A 1:2 mixture of [(S)-2](AuCl)2 [(S)-2 = (S)-3,5-t-Bu-4-MeO-MeOBIPHEP] and AgBF4 catalyzes the stereoconvergent, intermolecular enantioselective hydroamination of chiral, racemic 1,3-disubstituted allenes with N-unsubstituted carbamates to form N-allylic carbamates in good yield, with high regio- and diastereoselectivity, and up to 92% ee.
Gold und Silber: Eine 1:2‐Mischung von [{(S)‐1}(AuCl)2] und AgBF4 katalysiert die enantioselektive Hydroaminierung von chiralen racemischen 1,3‐disubstituierten Allenen mit N‐unsubstituierten Carbamaten, wobei N‐Allylcarbamate in guter Ausbeute, mit hoher Regio‐ und Diastereoselektivität und bis zu 92 % ee gebildet werden (siehe Schema; Cbz=Benzyloxycarbonyl).
Gold(I)-Catalyzed Stereoconvergent, Intermolecular Enantioselective Hydroamination of Allenes. -The reaction of disubstituted chiral and racemic allenes with N-unsubstituted carbamates provides N-allylic carbamates in good yields and with high enantioselectivities. The method is not only applicable to aryl butadienes, dialkyl allene (IVd) smoothly gives the desired product. -(BUTLER, K. L.; TRAGNI, M.; WIDENHOEFER*, R. A.; Angew. Chem., Int. Ed. 51 (2012) 21, 5175-5178, http://dx.doi.org/10.1002/anie.201201584 ; French Family Sci. Cent., Duke Univ., Durham, NC 27708, USA; Eng.) -S. Adam 38-036
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.