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Ring Enlargement and Sulfur-Transfer Processes in SiO2-Catalyzed Reactions of Thiocarbonyl Compounds with Optically Active Oxiranes.

✍ Scribed by Sergej Malaschichin; Changchun Fu; Anthony Linden; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2006
Weight
26 KB
Volume
37
Category
Article
ISSN
0931-7597

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✦ Synopsis

Abstract

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## Abstract The reactions of 1,3‐dioxolane‐2‐thione (**3**) with (__S__)‐2‐methyloxirane ((__S__)‐**1**) and with (__R__)‐2‐phenyloxirane ((__R__)‐**2**) in the presence of SiO~2~ in anhydrous dichloroalkanes led to the optically active spirocyclic 1,3‐oxathiolanes **8** with Me at C(7) and **9** w

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The reactions of the enolizable thioketone (1R,4R)-thiocamphor ( (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-thione; 1) with (S)-2-methyloxirane (2) in the presence of a Lewis acid such as SnCl 4 or SiO 2 in anhydrous CH 2 Cl 2 led to two diastereoisomeric spirocyclic 1,3-oxathiolanes 3 and 4 wit