Pre-equilibration of an interconverting set of isomeric allylic azides is coupled with an intramolecular Schmidt reaction to afford substituted lactams stereoselectively. The effect of substitution and a preliminary mechanistic study are reported. The synthetic potential of this method is demonstrated in the context of an enantioselective synthesis of an advanced intermediate leading toward pinnaic acid.
Pre-equilibration of an interconverting set of isomeric allylic azides is coupled with an intramolecular Schmidt reaction to afford substituted n class="Chemical">lactams stereoselectively. The effect of substitution and a preliminary mechanistic study are reported. The synthetic potential of this method is demonstrated in the context of an enantioselective synthesis of an advanced intermediate leading toward pinnaic acid.
Authors: Morgan M Walker; Shuming Chen; Brandon Q Mercado; K N Houk; Jonathan A Ellman Journal: Angew Chem Int Ed Engl Date: 2018-04-26 Impact factor: 15.336
Authors: Kevin J Frankowski; Ruzhang Liu; Gregory L Milligan; Kevin D Moeller; Jeffrey Aubé Journal: Angew Chem Int Ed Engl Date: 2015-09-01 Impact factor: 15.336
Authors: Amy A Ott; Mary H Packard; Manuel A Ortuño; Alayna Johnson; Victoria P Suding; Christopher J Cramer; Joseph J Topczewski Journal: J Org Chem Date: 2018-06-14 Impact factor: 4.354