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Ye, Z.-S., Science of Synthesis Knowledge Updates, (2021) 2, 304.
Electroreduction of diimines 10, which are prepared from 1,2-diamines and aromatic aldehydes, delivers trans-2,3-diarylpiperazine products 11 by intramolecular coupling (Scheme 3).[15,16] This method is remarkably effective for the construction of chiral tri- and tetrasubstituted piperazines when chiral diimines are employed. Additionally, diketoimine 10 (R1 = R2 = H; R3 = Me; Ar1 = Ph) is also suitable for this transformation and forms the desired product in 20% yield.
Meeeee 8 Meeeeeeee ee Meeeeeeeeee ee Meeeeeeeeeeeeeee Meeeeeeeeee[88,88]
M8 | M8 | M8 | Me8 | Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|---|---|
M | M | M | Me | Me+|Me eeeeeeeee, eeeee | 88 | [88] |
M | M | M | Me | Me eeeeeee/M eee eeeee, MeMM, MMM | 88 | [88] |
M | M | M | 8-MeMM8M8 | Me eeeeeee/M eee eeeee, MeMM, MMM | 88 | [88] |
M | M | M | 8-MeMM8M8 | Me eeeeeee/M eee eeeee, MeMM, MMM | 88 | [88] |
M | M | M | 8-MeM8M8 | Me eeeeeee/M eee eeeee, MeMM, MMM | 88 | [88] |
M | M | M | 8-MMM8M8 | Me eeeeeee/M eee eeeee, MeMM, MMM | 88 | [88] |
M | M | M | 8-MeM8MM8M8 | Me eeeeeee/M eee eeeee, MeMM, MMM | 88 | [88] |
M | M | M | 8-eeeeeeee | Me eeeeeee/M eee eeeee, MeMM, MMM | 88 | [88] |
Me | M | M | Me | Me eeeeeee/M eee eeeee, MeMM, MMM | 88 | [88] |
Me (M) | M | M | Me | Me eeeeeee/M eee eeeee, MeMM, MMM | 88 | [88] |
eMe (M) | M | M | Me | Me eeeeeee/M eee eeeee, MeMM, MMM | 88 | [88] |
eMe (M) | M | M | 8-MMM8M8 | Me eeeeeee/M eee eeeee, MeMM, MMM | 88 | [88] |
(MM8)8 | M | Me | Me eeeeeee/M eee eeeee, MeMM, MMM | 88e | [88] | |
(MM8)8 | M | 8-MMM8M8 | Me eeeeeee/M eee eeeee, MeMM, MMM | 88e | [88] | |
(MM8)8 | M | 8-MeMM8M8 | Me eeeeeee/M eee eeeee, MeMM, MMM | 88e | [88] | |
M | M | Me | Me | Me eeeeeee/M eee eeeee, MeMM, MMM | 88 | [88] |
e Mee (8M,8M)-8,8-eeeeeeeeeeeeeeeeee eee eeee eee eee eeeeeeee.
Meeeeeeeeeee Meeeeeeee
8,8-Meeeeeeeeeeeeeeeee (88, M8 = M8 = M8 = M; Me8 = Me); Meeeeee Meeeeeeee:[88]
M eeee ee Me8MMMe (8 e) ee MMM (88 eM) eee eee eeee e eeeeeee eeee (88-eM eeeeee) eeeeeeee eeee e Me eeeeeee (8 × 88 ee8), e eeeeee eee eeeee, eee e eeeeeee eeeeeeeee. Meeeeee 88 (M8 = M8 = M8 = M; Me8 = Me; 88 eeee) eee MeMM (88 eeee) eeee eeeee ee eee eeeeeeeee. Meeeeeeeeee eee eeeeee eeeeeee eee eeee eeee e eeeeeeee eeeeeee ee 8.8 M (8.8 M·eee−8), eee eeee eee eeeeeeeee eee eeeeee eeee M8M (888 eM). MeMMM8 eee eeeee ee eeeeee eee eM ee 8 eee eee eeeeeee eee eeeeeeeee eeee MM8Me8. Mee eeeeeee eee eeeeeeeeeeee eee eee eeeee eeeeeee eee eeeeeeeeeeeeee (eeeeee/MeMMe); eeeee: 8.88 e (88%); ee 88–88 °M.
References
[15] | Meee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[16] | Meeee, M.; Meee, M.; Meeeeeeee, M.; Meeeeeeee, M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888. |