title: Catalyst-directed diastereo- and site-selectivity in successive nucleophilic and electrophilic allylations of chiral 1,3-diols: protecting-group-free synthesis of substituted pyrans.
abstract: The iridium-catalyzed, protecting group-free synthesis of 4-hydroxy-2,6-cis- or trans-pyrans through successive nucleophilic and electrophilic allylations of chiral 1,3-diols occurs with complete levels of catalyst-directed diastereoselectivity in the absence of protecting groups, premetallated reagents, or discrete alcohol-to-aldehyde redox reactions.
authors.affiliation: University of Texas at Austin, Department of Chemistry, 1 University Station - A5300, Austin, TX 78712-1167 (USA).
authors.forename: Inji
authors.initials: I
authors.lastname: Shin
authors.forename: Gang
authors.initials: G
authors.lastname: Wang
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Krische
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D007495:Iridium / Q000737:chemistry; D010084:Oxidation-Reduction; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D011714:Pyrans; D007495:Iridium
keywords: catalyst-directed diastereoselectivity; polyketides; protecting group-free reactions; pyran; transfer hydrogenation