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Please login to access the full content or check if you have access via Mannich Reaction of Other Imines: N-Alkylimines, Cyclic Imines, and Ketimines

DOI: 10.1055/sos-SD-204-00021

Benohoud, M.; Hayashi, Y.Science of Synthesis: Asymmetric Organocatalysis, (20121126.

Less common imines such as N-alkylimines, cyclic imines, and imines derived from ketones (ketimines) have also been investigated as acceptors in the organocatalyst-mediated Mannich reaction of carbonyl compounds. The enantioselective Mannich reaction of ketimines is very limited, although the substrates would constitute an interesting template for the synthesis of quaternary β-amino carbonyl compounds.

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M8 eee (%) Meeee (%) ee 888 Mee
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MM8MMMMMM 88 88 [‌88‌]

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Meeeee 88 Meeeeee Meeeeeee ee Meeeeeeee eeee Meeeeeeee Meeeeeeee ee e Meeeee Meeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 M8 eee [(M,M)/(M,M)] eee (%) Meeeee (%) Mee
eMe M M M >88:8 88 88 [‌888‌]
eMe M M Me 8:8 88 88 [‌888‌]
eMe M M MMe 8:8 88 88 [‌888‌]
eMe M M M 88:8 88 88 [‌888‌]
eMe M MMe M >88:8 88 88 [‌888‌]
eMe (MM=MM)8 M >88:8 88 88 [‌888‌]
Me M M M 8:8 88 88e [‌888‌]
MM8MM=MM8 M M M 8:8 88 88e [‌888‌]

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Meeeee 88 eeee-Meeeeee Meeeeeee ee Meeeeee Meeeeee eee Meeeee Meeeee Meeeeeeee ee (M)-Meeeeee[‌888‌]

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M8 M8 eee (eeee/eee) eee (%) Meeeee (%) Mee
(MM8)8 >88:8 >88 88 [‌888‌]
(MM8)8 >88:8 88 88 [‌888‌]
Me M >88:8 >88 88 [‌888‌]
Me Me 88:8 >88 88 [‌888‌]
M M 88 88 [‌888‌]
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Meeeee 88 Meeeeee Meeeeeee ee β-Meeeeeeee Meeeeeeeeee eee Meeeeee Meeeeeeee ee (M)-Meeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-(Meeeeeeeeeeee) Meeeeeee 888; Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee eeeeeeee 88 (8.88e, 8eeee) ee e 8M eeee ee MeMe ee MMM (8eM) ee 88°M eee eeeee e eeee ee MeMM (88µM, 8eeee) ee e 8M eeee ee MeMe ee MMM (8eM). Mee eeeeeeee (88eeee) eee eeeee, eee eee eeeeeee eee eeeeeee eee e eeeeee, eeeeeeee ee eee eeeeeeee ee (eeeeeeeeeeeee)eeeeee eeeeee eeeee (888; 8.88eM, 8eeee). Mee eeeeeee eee eeeeeee ee 88°M eee 8e. Mee eeeeeeee eee eeeeeee ee eeee ee eeeeeeee ee MeMM8 (8.88e, 88eeee) eee MeMM (88eM). Mee eeeeeee eee eeeeeee eee e eeeeee ee 88°M eee ee 8°M eee eeeeeee 88eee. Mee eeeeeee eee eeeeeeee eeee eee. MM8Me (88eM) ee 8°M eee eeeeeeeee eeee Me8M (8×888eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee M8M (88eM) eee eeeee (88eM) eee eeeee (MeMM8), eee eee eeeeeee eee eeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:88); eeeee: 8888%; 8888% ee.

8,8-Meeeeeeeeeeeeeeee-8-eeee 888; Meeeeee Meeeeeeee:[‌888‌]

Me e eeee ee 8,8-eeeeeeee-8,8-eeeeeee-8M-8,8-eeeeee-8-eee (888; 8 eeeee) ee eeeee MMMM (8.8M) eee eeeee (M)-eeeeeee (8; 8.8 eeeee) eee eee eeeeee (8 eeeee). Mee eeeeeee eee eeeeeee eee 88e eee eeeeee eeee e eeeeeeeeee eeeeee eeeeeeeeee eeeeeee/MeMMe (8:8) eee eeee-eeeee MM8Me eeee. Mee eeeeeee eeeeeeee eee eeeeeeeee eeee eeeeeee/MeMMe (8:8; 8×). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8) eee eee eeeeeee eee eeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee MMMM (eeeeeeee eeeeeee/Me8M) eeeeeeeee eee eeeeeee ee e eeeee eeeeeeeeeee eeeee. Meeeeeeeeee eeeeeeeeee eeeeeeeeeeee eee eeee eeeeeeee eee eeeeeeeeeeeeeeeee (MM8Me8/eeeeee) ee eee eeeee eeeeeeee ee eeeeeeeeeeeee ee e eeeeee eeeeeeeeee eeeee eeeeeeeeeeeeeee eeeeee; eeeee: 8888%; 88 ee >88% ee.