Science of Synthesis

Aggarwal, V. K.; McGarrigle, E. M.; Shaw, M. A., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 336.

An alternative way to achieve enantiocontrol is through the use of chiral sulfides in the formation of the ylides. As well as avoiding the use of a chiral group on the substrate, which must often later be removed, this technique can allow the use of catalytic amounts of the chiral sulfide. Generally, however, good enantioselectivities are limited to the semistabilized class of ylides. Sulfide ‌15‌ can be used catalytically in the carbene-based system described in Section ‌2.6.1.1.1‌,[‌81‌] employing safer N-tosylhydrazone salts to generate the diazo compounds in situ rather than using stoichiometric diazo compounds, and forming trans-aziridines ‌50‌ (‌Scheme 29‌).[‌85‌]

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Meeeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

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8-Meeeeeeeeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

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References