Diastereomers of N-α-phenylethyl-t-butylsulfinamide:: Absolute configurations and predominant conformations
Diastereomers of N-α-phenylethyl-t-butylsulfinamide:: Absolute configurations and predominant conformations
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DOI：
10.1021/jo702544g
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发表时间：
2008-04-18
影响因子：
3.6
通讯作者：
Balinska, Agnieszka
中科院分区：
文献类型：
--
作者：
Petrovic, Ana G.;Polavarapu, Prasad L.;Balinska, Agnieszka
n -苯基乙基-t-丁基亚胺是一种复杂的分子立体化学体系，因为有许多确定绝对构型和主要构象的可能性。本文合成了由(-)-(S)- -苯乙基胺衍生的n -苯乙基-t-丁基亚胺的两种非对映体：(+)-非对映体和(-)-非对映体，并测定了它们的实验热光谱性质。这些性质包括振动圆二色性、电子圆二色性和光学旋转色散。利用这些实验数据，结合相应的密度泛函理论预测，确定了这两种非对映体的绝对构型和主要构象。此外，(-)-非对映体的绝对构型也由x射线衍射数据独立确定。
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.