113010-21-2Relevant academic research and scientific papers
Direct, intermodular, enantioselective, iridium-catalyzed allylation of carbamates to form carbamate-protected, branched allylic amines
Weix, Daniel J.,Markovic, Dean,Ueda, Mitsuhiro,Hartwig, John F.
supporting information; experimental part, p. 2944 - 2947 (2009/12/05)
The direct reaction between carbamates and achiral allylic carbonates to form branched, conveniently protected primary allylic amines with high regioseiectivity and enantioselectivity Is reported. This process occurs without base or with 0.5 equiv K3PO4 In the presence of a metalacyclic iridium catalyst containing a labile ethylene ligand. The reactions of aryl-, heteroaryl-, and alkyl-substituted allylic carbonates with BocNH 2, FmocNH2, CbZNH2, TrocNH2, TeocNH2, and 2-oxazolidinone occur In good yields, with high selectivity for the branched isomer and high enantioselectivities (98% average ee).
A Synthesis of Protected Aminoalkyl Epoxides from α-Amino Acids
Luly, Jay R.,Dellaria, Joseph F.,Plattner, Jacob J.,Soderquist, Jeffrey L.,Yi, Nwe
, p. 1487 - 1492 (2007/10/02)
The synthesis of alkylamino epoxides C is presented.Key steps include the synthesis of amino aldehyde 5 by reduction (DIBAH) of ester 3 or by oxidation of N-protected amino alcohol 4, both edducts of which are derived from amino acids.A study of the olefination of aldehyde 5 with unstabilized ylides is presented, and protected allylic amino 6, obtained in good to excellent optical purity, is oxidized (MCPBA) to epoxide C.Threo selectivity is observed in the epoxidation reaction.
