144397-85-3Relevant articles and documents
Enantioselective cyanation/brook rearrangement/C-acylation reactions of acylsilanes catalyzed by chiral metal alkoxides
Nicewicz, David A.,Yates, Christopher M.,Johnson, Jeffrey S.
, p. 6548 - 6555 (2007/10/03)
New catalytic enantioselective cyanation/1,2-Brook rearrangement/C- acylation reactions of acylsilanes (4) with cyanoformate esters (7) are described. The products of the reaction are fully substituted malonic acid derivatives (8). Catalysts for this transformation were discovered via a directed candidate screen of 96 metal-ligand complexes. Optimization of a (salen)aluminum complex revealed significant remote electronic effects and concentration effects. The scope of the reaction was investigated by using a number of aryl acylsilanes and cyanoformate esters. Chemoselective reduction of the reaction products (8) afforded new enantioenriched α-hydroxy-α- aryl-β-amino acid derivatives (32-34) and β-lactams (35 and 36). This reaction provides a simple method for the construction of new nitrogen-containing enantioenriched chiral building blocks.
Synthesis of carbonates and related compounds from carbon dioxide via methanesulfonyl carbonates
Bratt, Mark O.,Taylor, Paul C.
, p. 5439 - 5444 (2007/10/03)
Carbonate anions resulting from reaction of primary or secondary alcohols with carbon dioxide, when added to methanesulfonic anhydride in cooled acetonitrile solution, yield methanesulfonyl carbonates, a new class of synthetic intermediate. Base-mediated reaction of the methanesulfonyl carbonates with alcohols, thiols, and amines yields carbonates, thiocarbonates, and carbamates, respectively. Overall yields for the three steps vary from 19% to 42%.
Replacement of Phosgene with Carbon Dioxide: Synthesis of Alkyl Carbonates
McGhee, William,Riley, Dennis
, p. 6205 - 6207 (2007/10/03)
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