title: Deuterium-isotope study on the reductive ring opening of benzylidene acetals.
abstract: Specific deuterated reference compounds were prepared to probe the stereoselectivity of the reductive ring opening of carbohydrate-based benzylidene-type acetals. AlD(3) revealed a retentive stereoselectivity probably through the rare S(N)i (internal nucleophilic substitution) mechanism. An S(N)1-like mechanism occurs in the acid-promoted regioselective BD(3)·THF- or Et(3)SiD-reductive ring opening.
authors.affiliation: Genomics Research Center, Academia Sinica, Taipei 115, Taiwan.
authors.forename: I-Chi
authors.initials: IC
authors.lastname: Lee
authors.forename: Medel Manuel L
authors.initials: MM
authors.lastname: Zulueta
authors.forename: Chi-Rung
authors.initials: CR
authors.lastname: Shie
authors.forename: Susan D
authors.initials: SD
authors.lastname: Arco
authors.forename: Shang-Cheng
authors.initials: SC
authors.lastname: Hung
mesh_terms: D000080:Acetals / Q000737:chemistry*; D017607:Aluminum Compounds / Q000737:chemistry; D001597:Benzylidene Compounds / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D003903:Deuterium / Q000737:chemistry*; D006031:Glycosylation; D006878:Hydroxides / Q000737:chemistry; D018020:Lithium Compounds / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D017607:Aluminum Compounds; D001597:Benzylidene Compounds; D006878:Hydroxides; D018020:Lithium Compounds; C042073:lithium aluminum hydride; C031356:hydroxide ion; D003903:Deuterium