title: Complementary stereochemical outcomes in proline-based self-regenerations of stereocenters.
abstract: Stereoselective alkylations of proline-based amino amides are described, where high levels of either a cis or trans configuration can be attained simply by the choice of the aminal group. Isobutryaldehyde-derived aminals provide the cis configuration, while 1-naphthaldehyde-derived aminals engender the complementary trans configuration.
authors.affiliation: Department of Chemistry, Colorado State University , Fort Collins, Colorado 80523, United States.
authors.forename: Brian J
authors.initials: BJ
authors.lastname: Knight
authors.forename: Erin E
authors.initials: EE
authors.lastname: Stache
authors.forename: Eric M
authors.initials: EM
authors.lastname: Ferreira
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000478:Alkylation; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007093:Imidazoles / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000577:Amides; D007093:Imidazoles; D009281:Naphthalenes; C009840:1-naphthaldehyde; D011392:Proline