title: Acceleration of Petasis reactions of salicylaldehyde derivatives with molecular sieves.
abstract: Mild reaction conditions for Petasis reactions of substituted salicylaldehydes with various amines and arylboronic acids in the presence of molecular sieves were developed. Molecular sieves (MS) significantly accelerated the reaction rates and drove the reactions to high conversions. The conditions were applied to the synthesis of the core structure of BIIB042, a γ-secretase modulator, without stereochemical erosion of a stereogenic center in the salicylaldehyde intermediate.
authors.affiliation: Biogen Idec, 14 Cambridge Center, Cambridge, Massachusetts 02142, USA. Xianglin.shi@biogenidec.com
authors.forename: Xianglin
authors.initials: X
authors.lastname: Shi
authors.forename: Dominique
authors.initials: D
authors.lastname: Hebrault
authors.forename: Michael
authors.initials: M
authors.lastname: Humora
authors.forename: William F
authors.initials: WF
authors.lastname: Kiesman
authors.forename: Hairuo
authors.initials: H
authors.lastname: Peng
authors.forename: Tina
authors.initials: T
authors.lastname: Talreja
authors.forename: Zezhou
authors.initials: Z
authors.lastname: Wang
authors.forename: Zhili
authors.initials: Z
authors.lastname: Xin
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D053829:Amyloid Precursor Protein Secretases; D060326:Chemistry Techniques, Synthetic; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000588:Amines; C572522:BIIB042; C013243:salicylaldehyde; D053829:Amyloid Precursor Protein Secretases