Asymmetric Phase-Transfer Catalytic aza-Michael Addition to Cyclic Enone: Highly Enantioselective and Diastereoselective Synthesis of Cyclic 1,3-Aminoalcohols
Jaeyong Lee, Jeong Woo Ban, Jeongseok Kim, Sehun Yang, Geumwoo Lee, Lama Prema Dhorma, Mi‐Hyun Kim, Min Woo Ha, Suckchang Hong, Hyeung‐geun Park
Abstract
The highly enantioselective aza-Michael reaction of tert-butyl β-naphthylmethoxycarbamate to cyclic enones has been accomplished by using a new cinchona alkaloid derived C(9)-urea ammonium catalyst under phase-transfer catalysis conditions with up to 98% ee at 0 °C. The resulting aza-Michael adducts can be converted to versatile intermediates by selective deprotection and the cyclic 1,3-aminoalcohols by diastereoselective reduction with up to 32:1, which have been widely used as important pharmacophores in pharmaceutical development.
Topics & Concepts
Enantioselective synthesisChemistryCinchonaMichael reactionEnoneCatalysisCinchona AlkaloidsCombinatorial chemistryOrganic chemistryOrganocatalysisAsymmetric Synthesis and CatalysisChemical Synthesis and AnalysisAsymmetric Hydrogenation and Catalysis