Science of Synthesis

Mahrwald, R.; Schetter, B., Science of Synthesis, (2008) 36, 947.

Metalated dithianes are used as valuable tools for constructing C—C bonds via “Umpolung” reactions.[‌603‌,‌604‌] The use of epoxides as electrophiles is a particularly attractive feature of dithiane chemistry and provides an effective alternative to aldol additions.[‌605‌] It is well established that the ring opening of epoxides proceeds via an SN2 process and, in general, epoxides react with lithiated dithianes (as acyl equivalents) at the less sterically hindered carbon atom. Functionalities near the epoxide group may enhance existing regio- and stereochemical preferences.

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References

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• 8.Meeeee-Meee, (8888) 8/8e, 8888.
• 8.Meeeee-Meee, (8888) M 8, 888.
• 8.Meeeee-Meee, (8888) M 88e, 888.