title: Generation of stereochemically defined tetrasubstituted enolborinates by 1,4-hydroboration of α,β-unsaturated morpholine carboxamides with (diisopinocampheyl)borane.
abstract: On all fours: The title reaction with (Ipc)2 BH provides tetrasubstituted enolborinates which undergo aldol reactions with aldehydes to form products with all-carbon quaternary centers with exceptional diastereo- and enantioselectivity. A change to the substitution pattern of the starting amide leads to either diastereomer of the α-methyl-α-ethyl-β-hydroxy carboxamide (1 or 2).
authors.affiliation: Department of Chemistry The Scripps Research Institute 130 Scripps Way, 3A2, Jupiter FL 33458 (USA).
authors.forename: Christophe
authors.initials: C
authors.lastname: Allais
authors.affiliation: Department of Chemistry The Scripps Research Institute 130 Scripps Way, 3A2, Jupiter FL 33458 (USA).
authors.forename: Andy S
authors.initials: AS
authors.lastname: Tsai
authors.affiliation: Department of Chemistry The Scripps Research Institute 130 Scripps Way, 3A2, Jupiter FL 33458 (USA).
authors.forename: Philippe
authors.initials: P
authors.lastname: Nuhant
authors.affiliation: Department of Chemistry The Scripps Research Institute 130 Scripps Way, 3A2, Jupiter FL 33458 (USA).
authors.forename: William R
authors.initials: WR
authors.lastname: Roush
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D001896:Boron Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D009025:Morpholines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C587231:(diisopinocampheyl)borane; D000447:Aldehydes; D000577:Amides; D001880:Boranes; D001896:Boron Compounds; D009025:Morpholines; C037574:morpholine
keywords: amides; boron; enantioselectivity; enols; synthetic methods