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1.1.7.3.2 Enantioselective Aziridination Reactions

DOI: 10.1055/sos-SD-204-00129

MacMillan, D. W. C.; Watson, A. J. B.Science of Synthesis: Asymmetric Organocatalysis, (20121389.

Enantioenriched aziridines are highly versatile building blocks that are utilized extensively as precursors to a broad range of nitrogenous products including chiral amines and amino acids. Additionally, the aziridine motif is present within a number of bioactive natural products. The synthetic flexibility of aziridines has encouraged significant investigation into establishing enantioselective methods for their construction.[‌201‌‌203‌] General routes include stoichiometric chiral-pool methods based on either enantiopure starting materials or the use of chiral auxiliaries, while more modern catalytic asymmetric methods rely upon organometallic complexes and Lewis acids.

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Meeee Meeeeeee Meeeeeeee Meeeee Meeeeeeeee Meeeeee eee ee (%) Meeee (%) Mee
Meeeeeeee Meeee
8 8.8:8 88 (8.8 eeeee), MMMe8 (8.88M), 88°M 8:8 88 88 [‌888‌]
8 8.8:8 88 (8.8 eeeee), MMMe8 (8.88M), 88°M 8:8 88 88 [‌888‌]
8 8:8 88 (8.8 eeeee), MeMMe (8 eeeee), MM8Me8 (8.8M), 88°M >88:8 88e 88 [‌888‌]
8 8:8 88 (8.8 eeeee), MeMMe (8 eeeee), MM8Me8 (8.8M), 88°M >88:8 88e 88 [‌888‌]
8 8:8.8 88 (8.8 eeeee), MeMMe (8.8 eeeee), eeeeeee (8.8M), 8°M 88 88 [‌888‌]
8 8:8.8 88 (8.8 eeeee), MeMMe (8.8 eeeee), eeeeeee (8.8M), 8°M 88 88 [‌888‌]
8 8:8.8 88 (8.8 eeeee), (M)-MeeM(Me)MM8MM8M (8.8 eeeee), MeMMM8 (8 eeeee), MMMe8 (8.88M), 88°M 88:8 88 88 [‌888‌]
8 8:8.8 88 (8.8 eeeee), (M)-MeeM(Me)MM8MM8M (8.8 eeeee), MeMMM8 (8 eeeee), MMMe8 (8.88M), 88°M >88:8 88 88 [‌888‌]
8 8.8:8 88 (8.8 eeeee), (M)-MeeM(Me)MM8MM8M (8.8 eeeee), MeMMM8 (8 eeeee), MMMe8 (8.88M), 88°M e.e. 88 88 [‌888‌]
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Me e eeeeeee ee (M)-8-[eeeeeeee(eeeeeeeeeeeeeee)eeeeee]eeeeeeeeeee (88; 88.8ee, 8.88eeee, 8.8 eeeee) eee eeeeee eeeeeeeeeeeeeeee (88.8ee, 8.88eeee, 8 eeeee) ee MMMe8 (8eM) ee 88°M eee eeeee (M)-8-(8-eeeeeeeeeee)eeee-8-eeee (88.8ee, 8.8eeee, 8.8 eeeee). Mee eeeeeeeee eeeeeee eee eeeeeee ee 88°M eee 88eee eeeeee eeeee eeeeeeee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (MeMMe/eeeeeee ee MeMMe/eeeeeee); eeeee: 88.8ee (88%); ee 8:8; 88% ee. Mee eeeeeeeeeeee eeeeee eee eeeeeeeeee ee MMMM eeeeeeee [MM-M eeeeee, eMeMM/eeeeee 8:8, 8.8eM·eee8; eM (eeeee)=88.8eee, eM (eeeee)=88.8eee].

eeee-Meeee (M)-8-Meeee-8-eeeeeeeeeeeeeee-8-eeeeeeeeeee (Meeee 88, Meeee 8); Meeeeee Meeeeeeee:[‌888‌]

Me (M)-8-[eeeeeeee(eeeeeeeeeeeeeee)eeeeee]eeeeeeeeeee (88; 88.8ee, 8.88eeee, 8.8 eeeee) ee eeeeeee (8.8eM) ee 8°M eee eeeee 8-eeeeeeeeeeeee-8-eeee (88.8ee, 8.88eeee, 8 eeeee), eeee-eeeee (eeeeeeee)eeeeeeeee (88.8ee, 8.8eeee, 8.8 eeeee), eee MeMMe (88.8ee, 8.888eeee, 8.8 eeeee). Mee eeeeeeeee eeeeeee eee eeeeeee ee 8°M eee 88e eeeeee eeeee eeeeeeee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (MeMMe/eeeeeee); eeeee: 88.8ee (88%); 88% ee. Mee eeeeeeeeeeee eeeeee eee eeeeeeeeee ee MMMM eeeeeeee [MM-M eeeeee, eMeMM/eeeeee 8:88, 888ee, 8eM·eee8; eM (eeeee)=8.8eee, eM (eeeee)=8.8eee].

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References


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