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Nagasawa, K.; Sohtome, Y., Science of Synthesis: Asymmetric Organocatalysis, (2012) 2, 31.
1,4-Addition reactions of nitroalkenes with disubstituted phosphites serve as important methodologies for the preparation of β-aminophosphonic acid derivatives, which are attractive as peptidomimetics and therapeutic agents with a broad spectrum of biological activities.[43] Terada and co-workers reported a new technique for conducting highly enantioselective 1,4-addition reactions of nitroalkenes with diphenyl phosphite that relies on the use of the axially chiral guanidine catalyst 79 (Scheme 29).[44]
Me eee eeeeeee ee Meeeee 88 eeeeeeeeee, e eeeee eeeee ee eeeeeeeeeeee 88, eeeeeee eeeeeeee eeeeeeeeeeee eeeeee eeeeeee eeeeeeeeee eeeeeeeeee, eee ee eeee ee eeeeeeeeeeeeeeee 8,8-eeeeeeee eeeeeeeee eeeeeeee ee 8 eee% eeeeeeee ee 88. Meeee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeee 88 ee eeeeee eeeeeeeeeeee eeeeee eeee eeee eeeeeeeeeeeeeeeeeeee. Me eee eeeee ee eeeeeeee-eeeeeeeeeee eeeeeeeeeeee, eeeeeeee eee eeeeeeee eeeeeeeeeee (−88 °M) eee eeeeeeeeee eee eeeeeeee eeeeeee ee 8 eee% eee eeeeeeee ee eeeeee eeeeeeee ee eeee eeeeee eee eeeeeeeeeeeeeeeeeeee. Meeeeee, eeeee eeeeeeeeeeeeeeeeeeee eee eeeeeeee ee eeeeeeee ee eeeeeeeee-eeeeeeeeeee eeeeeeeeeeee.[88]
Meeeee 88 Meeeeeeeeeeeeeee 8,8-Meeeeeee Meeeeeeee ee Meeeeeee Meeeeeeee ee Meeeeeeeeeee Meeee e Meeeee Meeeeeeee Meeeeeee[88]
M8 | Meee (e) | Meeee (%) | ee (%) | Mee |
---|---|---|---|---|
Me | 8 | 88 | 88 | [88] |
8-MeMM8M8 | 8.8 | 88 | 88 | [88] |
8-MeM8M8 | 8 | 88 | 88 | [88] |
8-MeMM8M8 | 8 | >88 | 88 | [88] |
8-MeM8M8 | 8.8 | 88 | 88 | [88] |
8-M8MM8M8 | 8.8 | 88 | 88 | [88] |
8-eeeeeeee | 8.8 | >88 | 88 | [88] |
8-eeeee | 8 | 88 | 88e | [88] |
8-eeeeeee | 8.8 | 88 | 88e | [88] |
eMe | 8.8 | 88 | 88 | [88] |
Me | 8 | 88 | 88 | [88] |
(MM8)8Me | 8 | >88 | 88 | [88] |
e Mee eeeeeeee eee eeeeeee eee eeeee 8 eee% ee eeeeeeee ee 88 ee −88 °M.
Meeeeeeeeeee Meeeeeeee
Meeeeeee (M)-(8-Meeee-8-eeeeeeeeeee)eeeeeeeeeee (88, M8 = Me); Meeeeee Meeeeeeee:[88]
Me e eeeeeee ee (M)-8-eeeee-8-eeeeeeeeeeee (88, M8 = Me; 88.8 ee, 8.88 eeee) eee 8-Å eeeeeeeee eeeeee (88 ee) ee e-MeMMe (8.8 eM) eee eeeee eeeeeeee eeeeeeeee (88.8 µM, 8.88 eeee) ee ee. Meeee eee eeeeeee eee eeee eeeeeee eee 88 eee ee −88 °M, eeeeeeee 88 (8.88 ee, 8.888 eeee) eee eeeee eee eee eeeeeeeee eeeeeee eee eeeeeee eee 8 e. Meeee eeeeeeeeee ee eee eeeeeeee (MMM eeeeeeeeee), eee eeeeeee eee eeeeeee eeee eee. ee MM8Me eee eeeeeeee eeeeeee e eee ee Meeeee. Mee eeeeeeee eee eeeeeeeee eeee MeMMe eee eee eeeeeeee eeee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeeeee, eeeee eee eeeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee/MeMMe 8:8 ee 8:8); eeeee: 88%; 88% ee.
References
[43] | Meeeeeee, M.; Meeeee, M.; ee eee Meeeee, M. M., Meee. Mee., (8888) 888, 888. |
[44] | Meeeee, M.; Meeeeee, M.; Mee, M.; M. Me. Meee. Mee., (8888) 888, 88888. |