title: Copper-catalyst-controlled site-selective allenylation of ketones and aldehydes with propargyl boronates.
abstract: A practical and highly site-selective copper-PhBPE-catalyst-controlled allenylation with propargyl boronates has been developed. The methodology has shown to be tolerant of diverse ketones and aldehydes providing the allenyl adducts in high selectivity. The BPE ligand and boronate substituents were shown to direct the site selectivity for which either propargyl or allenyl adducts can be acquired in high selectivity. A model is proposed that explains the origin of the site selectivity.
authors: Chemical Development, Boehringer-Ingelheim Pharmaceuticals Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. keith.fandrick@boehringer-ingelheim.com
authors: Keith R
authors: KR
authors: Fandrick
authors: Junichi
authors: J
authors: Ogikubo
authors: Daniel R
authors: DR
authors: Fandrick
authors: Nitinchandra D
authors: ND
authors: Patel
authors: Jaideep
authors: J
authors: Saha
authors: Heewon
authors: H
authors: Lee
authors: Shengli
authors: S
authors: Ma
authors: Nelu
authors: N
authors: Grinberg
authors: Carl A
authors: CA
authors: Busacca
authors: Chris H
authors: CH
authors: Senanayake
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D000447:Aldehydes; D000466:Alkadienes; D001896:Boron Compounds; D007659:Ketones; D008024:Ligands; C025947:propadiene; D003300:Copper