title: Catalyst-Controlled Multicomponent Aziridination of Chiral Aldehydes.
abstract: A highly diastereoselective and enantioselective method for the multicomponent aziridination of chiral aldehydes has been developed with BOROX catalysts of the VANOL (3,3'-diphenyl-2,2'-bi-1-naphthol) and VAPOL (2,2'-diphenyl-(4-biphenanthrol)) ligands. Very high to perfect catalyst control is observed with most all substrates examined including aldehydes with chiral centers in the α- and β-positions. High catalyst control was also observed for a number of chiral heterocyclic aldehydes allowing for the preparation of epoxy aziridines, bis(aziridines) and ethylene diaziridines. Application of this reaction in the synthesis of β3-homo-d-alloisoleucine and β3-homo-l-isoleucine is reported.
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.
authors.forename: Munmun
authors.initials: M
authors.lastname: Mukherjee
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.
authors.forename: Yubai
authors.initials: Y
authors.lastname: Zhou
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.
authors.forename: Yijing
authors.initials: Y
authors.lastname: Dai
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.
authors.forename: AniL K
authors.initials: AK
authors.lastname: Gupta
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.
authors.forename: V Reddy
authors.initials: VR
authors.lastname: Pulgam
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.
authors.forename: Richard J
authors.initials: RJ
authors.lastname: Staples
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.
authors.forename: William D
authors.identifier: http://orcid.org/0000-0002-5668-4312
authors.initials: WD
authors.lastname: Wulff
keywords: asymmetric catalysis; aziridines; borox catalyst; catalyst control; vapol