title: (E)-2-boryl 1,3-dienes from the 10-TMS-9-BBDs: highly selective reagents for the asymmetric synthesis of anti-α,β-disubstituted β-allenylamines from the allylboration of aldimines.
abstract: The asymmetric allylboration of N-H aldimines with optically pure trans-4-substituted-2-boryl-1,3-dienes 6 is described. These organoboranes 6 serve as near-perfect asymmetric allylborating agents for N-H aldimines for the preparation of anti-1,2-disubstituted-3,4-pentadien-1-amines 11 as essentially single diastereomers in enantiomerically pure form (>98% de, ≥98% ee). Enantiomerically pure cis-2,3-disubstitued piperidines 12 and α,β-disubstituted-β-amino acids 17 are readily prepared through the standard protocols. A novel Ru-catalyzed hydroamination provides trans-4,5-disubstituted-1-pyrrolines 21 from 11.
authors.affiliation: Department of Chemistry, University of Puerto Rico , San Juan, Puerto Rico 00931-3346.
authors.forename: Javier R
authors.initials: JR
authors.lastname: González
authors.forename: John A
authors.initials: JA
authors.lastname: Soderquist
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D011090:Polyenes / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000588:Amines; D000596:Amino Acids; D001880:Boranes; D007202:Indicators and Reagents; D011090:Polyenes; D011759:Pyrrolidines; D012428:Ruthenium