Chiral sulfinates studied by optical rotation, ECD and VCD: the absolute configuration of a cruciferous phytoalexin brassicanal C.
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.
Taniguchi
Tohru
T
Department of Chemistry, Columbia University, New York, NY 10027, USA.
Monde
Kenji
K
Nakanishi
Koji
K
Berova
Nina
N
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
D001688:Biological Products; D007211:Indoles; D012717:Sesquiterpenes; D013441:Sulfinic Acids; D013729:Terpenes; C533802:brassicanal C; D014050:Toluene; D000094162:Phytoalexins