Science of Synthesis

Sweeney, J. B., Science of Synthesis, (2009) 40, 700.

With the development of the Sharpless asymmetric dihydroxylation process, nonracemic 1,2-diols are routinely available in high enantiomeric excess. These diols are smoothly converted into aziridines via cyclic sulfates.[‌330‌] Two processes are feasible for the conversion of cyclic sulfates into aziridines: using an amine nucleophile, cyclic sulfates ‌197‌ afford 1-substituted aziridines ‌198‌ (‌Scheme 119‌), while with an azide nucleophile cyclic sulfates afford 1-unsubstituted aziridines; sulfate ‌199‌, for example, affords aziridine ‌200‌ (‌Scheme 120‌).[‌330‌,‌331‌] Since the processes are stereospecific, the reaction allows the predictable conversion of alkenes into aziridines with retention of configuration, that is, trans-alkenes are converted into trans-aziridines, and cis-alkenes into cis-aziridines.

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‌Meeeeeeeeee 888‌

M8	M8	M8	ee (%)	Meeee (%)	Mee
Me	M	Me	>88	88	[‌888‌]
Me	M	(MM8)8Me	>88	88	[‌888‌]
Me	M		>88e	88	[‌888‌]
Me	Me	Me	88e,e	88	[‌888‌]
Me	Me	Me	>88e	88	[‌888‌]

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Meeeeeeeeeee Meeeeeeee 88

8-Meeeeeeeeee Meeeeeeeee ‌888‌; Meeeeee Meeeeeeee:[‌888‌]

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(M)-8-Meeeeeeeeeeeeeeeeee (‌888‌); Meeeeee Meeeeeeee:[‌888‌]

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References

Meeeeee Meeeeeeeeee

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