241487-22-9Relevant articles and documents
Enantioselective Synthesis of Caprolactam and Enone Precursors to the Heterocyclic DEFG Ring System of Zoanthenol
Bagdanoff, Jeffrey T.,Behenna, Douglas C.,Stockdill, Jennifer L.,Stoltz, Brian M.
, p. 2101 - 2104 (2016)
The enantioselective synthesis of both caprolactam and enone synthons for the DEFG ring system of zoanthenol are described. The evolution of this approach proceeds first through a synthesis using the chiral pool as a starting point. Challenges in protecting-group strategy led to the modification of this approach beginning with (±)-glycidol. Ultimately, an efficient approach was developed by employing an asymmetric hetero-Diels-Alder reaction. The caprolactam building block can be converted by an interesting selective Grignard addition into the corresponding enone synthon. Addition of a model alkyne provides support for the late-stage addition of a hindered alkyne to the caprolactam building block.
Acyloxy Rearrangement-Triggered Regioselective Hydration of ?-Acetoxy-α,β-Alkynoates/Halo Alkynes
Mendhekar, Kishor L.,Mohapatra, Debendra K.,Pradhan, Tapas R.
supporting information, p. 4881 - 4895 (2020/05/01)
Herein, we report a simple, efficient, highly regioselective, and broad-scope hydration method that is facilitated by an unusual interception of an electrophilic intermediate by water generated via acetate group participation during [3,3]-acyloxy rearrang
Double conjugate addition of dithiols to propargylic carbonyl systems to generate protected 1,3-dicarbonyl compounds
Sneddon, Helen F.,Van Den Heuvel, Alexandra,Hirsch, Anna K. H.,Booth, Richard A.,Shaw, David M.,Gaunt, Matthew J.,Ley, Steven V.
, p. 2715 - 2725 (2007/10/03)
The work describes the efficient double conjugate addition of ethane and propane dithiols in the presence of sodium methoxide to a wide variety of propargylic carbonyl containing compounds. The products of these reactions are differentiated, 1,3-dicarbony
