title: Highly enantioselective Mannich reactions with α-aryl silyl ketene acetals and imines.
abstract: Mannich reactions with chiral silicon Lewis acid activated acylhydrazones and α-aryl silyl ketene acetals and α-aryl,α-alkyl silyl ketene imines proceed efficiently and with good to excellent levels of both diastereoselectivity and enantioselectivity. The reactions provide access to α-aryl,β-hydrazido esters and α-aryl,α-alkyl,β-hydrazido nitriles, which are valuable analogs of β-amino acids.
authors.affiliation: Department of Chemistry, Columbia University, New York, New York 10027, USA.
authors.forename: Gregory T
authors.initials: GT
authors.lastname: Notte
authors.forename: Jenny M
authors.initials: JM
authors.lastname: Baxter Vu
authors.forename: James L
authors.initials: JL
authors.lastname: Leighton
mesh_terms: D000080:Acetals / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D004952:Esters; D005030:Ethylenes / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D017646:Organosilicon Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D000596:Amino Acids; D004952:Esters; D005030:Ethylenes; D007097:Imines; D007659:Ketones; D009570:Nitriles; D017646:Organosilicon Compounds; C008223:ketene