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40.1.8.1.1.1.1 Electroreductive Cyclization of Diimines

DOI: 10.1055/sos-SD-140-00314

Ye, Z.-S.Science of Synthesis Knowledge Updates, (20212304.

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]

Meeeeeeeeee 8

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.

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