title: Stereodivergent and regioselective synthesis of 3,4-cis- and 3,4-trans-pyrrolidinediols from alpha-amino acids.
abstract: [reaction: see text] Highly stereodivergent Woodward-Prevost reaction applied to iodoacetates derived from homochiral alpha-amino acids afforded enantiopure 3,4-cis- and 3,4-trans-pyrrolidinediol derivatives, with control over the protecting group, allowing for differential protection.
authors.affiliation: Division of Applied Life Science, BK21 program, Department of Agricultural Chemistry, Gyeongsang National University, Jinju 660-701, South Korea.
authors.forename: Jin Hyo
authors.initials: JH
authors.lastname: Kim
authors.forename: Marcus J C
authors.initials: MJ
authors.lastname: Long
authors.forename: Jun Young
authors.initials: JY
authors.lastname: Kim
authors.forename: Ki Hun
authors.initials: KH
authors.lastname: Park
mesh_terms: D000085:Acetates / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D003500:Cyclization; D007461:Iodoacetates / Q000138:chemical synthesis / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: C500185:3,4-pyrrolidinediol; D000085:Acetates; D000498:Allyl Compounds; D000596:Amino Acids; D007461:Iodoacetates; D011759:Pyrrolidines; C498551:allyl acetate