title: Synthesis and chiroptical properties of a novel C2-symmetric binaphthyl phosphortriamide ("chiral HMPA").
abstract: By use of an asymmetric Ullmann coupling involving chiral naphthalene oxazolines 1, the title compounds were prepared in good yields and with high diastereoselectivity. Hydrolysis of the binaphthyl oxazolines 2 led to the di-aldehydes 5, which were transformed into the azepine derivative, 6. The latter was treated with the appropriate phosphoryl halide to access the chiral HMPA systems 7 and 9. The CD spectra of the chiral azepine 6 and the chiral phosphoramides 7 and 9 were measured and showed a strong positive CD couplet near 225 nm, consistent with the P axial chirality (S configuration). Semi-empirical CNDO/S molecular orbital calculations of the CD spectrum of 6 satisfactorily reproduced the major features of the observed spectrum.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins 80523, USA.
authors.forename: A I
authors.initials: AI
authors.lastname: Meyers
authors.forename: T
authors.initials: T
authors.lastname: Nguyen
authors.forename: D
authors.initials: D
authors.lastname: Stoianova
authors.forename: N
authors.initials: N
authors.lastname: Sreerama
authors.forename: R W
authors.initials: RW
authors.lastname: Woody
authors.forename: A
authors.initials: A
authors.lastname: Koslowski
authors.forename: J
authors.initials: J
authors.lastname: Fleischhauer
mesh_terms: D002942:Circular Dichroism; D006492:Hempa / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007202:Indicators and Reagents; D009281:Naphthalenes; D006492:Hempa