title: Control of five contiguous stereogenic centers in an organocatalytic kinetic resolution via Michael/acetalization sequence: synthesis of fully substituted tetrahydropyranols.
abstract: An organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols via Michael/acetalization sequence to give fully substituted tetrahydropyranols is described. The process affords the products with high to excellent stereoselectivities (up to 19.9:1.5:1 dr and 98% ee). The highly enantioenriched, less reactive (S)-nitroallylic alcohols 3 were isolated with good to high chemical yields (30-44%). The synthetic application of the resolved substrate is shown toward the synthesis of enantioenriched (+)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutyric acid.
authors.affiliation: Department of Chemistry, National Taiwan Normal University , Taipei 11677, Taiwan.
authors.forename: Ramani
authors.initials: R
authors.lastname: Gurubrahamam
authors.forename: You-Song
authors.initials: YS
authors.lastname: Cheng
authors.forename: Kwunmin
authors.initials: K
authors.lastname: Chen
mesh_terms: D000438:Alcohols; D002384:Catalysis; D003500:Cyclization; D007700:Kinetics; D015394:Molecular Structure; D010654:Phenylbutyrates / Q000138:chemical synthesis* / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D010654:Phenylbutyrates; D011714:Pyrans; C034940:3-amino-2-hydroxy-4-phenylbutanoic acid