Stratmann O, Kaiser B, Fröhlich R, Meyer O, Hoppe D
Organisch-Chemisches Institut der Universität Westfälische Wilhelms-Universität Münster, Germany.
Chemistry. 2001 Jan 19;7(2):423-35. doi: 10.1002/1521-3765(20010119)7:2<423::aid-chem423>3.0.co;2-y.
The lithium compound (S)-7, formed by deprotonation of the (S)-S-1-phenylethyl thiocarbamate (S)-10, is configurationally stable at -70 degrees C. Even at elevated temperatures it racemizes only very slowly. It represents the first essentially enantiopure alpha-thiocarbanion derivative and can be utilized in asymmetric synthesis. Most electrophiles (except proton acids) add to (S)-7 with complete stereoinversion. Cleavage of the substitution products leads to practically enantiopure, tertiary 1-phenylalkanethiols.
由（S）-S-1-苯乙基硫代氨基甲酸酯（S）-10去质子化形成的锂化合物（S）-7在-70℃下构型稳定。即使在升高的温度下，它的外消旋化也非常缓慢。它是第一个基本对映体纯的α-硫代碳负离子衍生物，可用于不对称合成。大多数亲电试剂（质子酸除外）以完全立体反转的方式加成到（S）-7上。取代产物的裂解产生几乎对映体纯的叔1-苯基链烷硫醇。
