title: Chiral sulfinates studied by optical rotation, ECD and VCD: the absolute configuration of a cruciferous phytoalexin brassicanal C.
abstract: The optical rotation, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) of chiral sulfinates have been studied experimentally, and analysed by density functional theory calculation, aiming at establishing a reliable and convenient methodology to determine their absolute configuration. Through the study on a model chiral sulfinate with known absolute configuration, (R)-(+)-methyl p-toluenesulfinate ((R)-(+)-1), each technique was found to be reliable in assigning chirality of sulfinates. We then applied these methods to a synthetically prepared cruciferous phytoalexin, brassicanal C ((-)-2), and unambiguously determined its absolute configuration as S. The advantages and disadvantages of each spectroscopy on sulfinates are also discussed.
authors.affiliation: Department of Chemistry, Columbia University, New York, NY 10027, USA.
authors.forename: Tohru
authors.initials: T
authors.lastname: Taniguchi
authors.forename: Kenji
authors.initials: K
authors.lastname: Monde
authors.forename: Koji
authors.initials: K
authors.lastname: Nakanishi
authors.forename: Nina
authors.initials: N
authors.lastname: Berova
mesh_terms: D001688:Biological Products / Q000737:chemistry; D002942:Circular Dichroism; D004583:Electrons; D007211:Indoles / Q000737:chemistry*; D008968:Molecular Conformation; D009904:Optical Rotation; D011789:Quantum Theory; D012717:Sesquiterpenes; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000737:chemistry*; D013729:Terpenes / Q000737:chemistry*; D014050:Toluene / Q000737:chemistry; D000094162:Phytoalexins
chemical_list: D001688:Biological Products; D007211:Indoles; D012717:Sesquiterpenes; D013441:Sulfinic Acids; D013729:Terpenes; C533802:brassicanal C; D014050:Toluene; D000094162:Phytoalexins