title: Diastereomers of N-alpha-phenylethyl-t-butylsulfinamide: absolute configurations and predominant conformations.
abstract: N-alpha-Phenylethyl-t-butylsulfinamide is a complicated system for determining molecular stereochemistry because of numerous possibilities for assigning the absolute configuration and a predominant conformation. Two diastereomers of N-alpha-phenylethyl-t-butylsulfinamide derived from (-)-(S)-alpha-phenylethyl amine, a (+)-diastereomer and a (-)-diastereomer, have been synthesized and their experimental chiroptical spectroscopic properties have been measured. These properties include vibrational circular dichroism, electronic circular dichroism and optical rotatory dispersion. Using these experimental data, in conjunction with corresponding density functional theoretical predictions, the absolute configuration and predominant conformations of these two diastereomers have been determined. Also, the absolute configuration of (-)-diastereomer has been independently confirmed by determining its structure from X-ray diffraction data.
authors.affiliation: Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA.
authors.forename: Ana G
authors.initials: AG
authors.lastname: Petrovic
authors.forename: Prasad L
authors.initials: PL
authors.lastname: Polavarapu
authors.forename: Jozef
authors.initials: J
authors.lastname: Drabowicz
authors.forename: Piotr
authors.initials: P
authors.lastname: Lyzwa
authors.forename: Marian
authors.initials: M
authors.lastname: Mikołajczyk
authors.forename: Wanda
authors.initials: W
authors.lastname: Wieczorek
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Balińska