Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.
2.5.6.1.2 Asymmetric Direct Reductive Amination of β-Keto Amides

DOI: 10.1055/sos-SD-202-00095

Xu, L.; Wu, X.; Xiao, J.Science of Synthesis: Stereoselective Synthesis, (20112291.

β-Amino amides are important intermediates in drug synthesis. Asymmetric direct reductive amination of β-keto amides allows direct access to such compounds and so would be more efficient than asymmetric hydrogenation of β-enamine amides.[‌115‌‌118‌] Simple ammonium salts as the nitrogen source are particularly attractive from an environmental and economical viewpoint.[‌119‌]

Mee eeeeeeeee eeeeeeee [Me(MMe)8(88)] ee eeeeee eeeeeeeee ee eeee eeeeeeee.[‌888‌] Meee, eeeeeeeee eeeeeeeeeee β-eeee eeeeee eee eeeeeeee ee eeee eee β-eeeee eeeeee 88 ee eeee eeeeee eee eeeeeeeee eeeeeeeeeeee eeeeeeee ee 88°M eee 88eee eeeeeeee ee eeeeeeeee eeeeeeee (Meeeee 88). Meeeeeee eeeeeeeeee eeeeee ee ee eeeeeeeeeeee eeeeeeeee, ee eeeee eeeeee, eeee ee eeeeeee, eeeeeeee, eee eeeeeee eeee ee eeeee eeeeee eee/ee eeeeeeeeeeeeeeeeeeee. Meee eeeeeeeeeeeeeeeeee ee eee eeeeeeeeee ee eee MMMMMMM eeeeee 88; eeeee eeeeee eeeeeeeeeeee eeee ee 8,8-eee(eeeeeeeeeeeeeeeee)-8,8-eeeeeeeeee eee 88 (eee Meeeee 88) eee eeee eeeeee.

Meeeee 88 Meeeeeeeee Meeeee Meeeeeeee Meeeeeeee ee β-Meee Meeeee eeee Meeeeeee Meeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 Meee (e) ee (%) Meeee (%) Mee
Me MMMe 88 88.8 88 [‌888‌]
Me MMMe 88 88.8 88 [‌888‌]
eMe MMMe 88 88.8 88 [‌888‌]
Me MMMe 88 88.8 88 [‌888‌]
8-MeMM8M8 MMMe 88 88.8 88 [‌888‌]
8-MM8M8 MMMe 88 88.8 88 [‌888‌]
Me eeeeeeeeee 88 88.8 88 [‌888‌]
8-eeeeeee MMMe 88 88.8 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

β-Meeee Meeeee 88; Meeeeee Meeeeeeee eee Meeeeeeeee Meeeee Meeeeeeee Meeeeeeee ee β-Meee Meeeee eeee Meeeeeee Meeeeeeeee:[‌888‌]

Me e 888-eM eeeeeeeee eeeee eeeeeeeee eeeeeeee eeee e eeeee eeeee eee e Meeeee-eeeeee eeeeeee eee eeee eeeeee [Me(MMe)8(88)] (88.8ee, 8.888eeee), β-eeee eeeee (8.88eeee), eee eeeeeeee eeeeeeeeee (8.888e, 88.88eeee). Mee eeeeeeeeee eee eeeeeeee eeee M8(e), eeeeeeee ee eeeeeeee ee MeMM (8eM). M8 eee eeeeeeeee eeeeeeeeee eeee eee eeeeeeeee ee e eeeeeeee ee 88eee, eeeeee eeeee eeeeeee ee 8eee ee eeeeeeeee eeeeeeeee eee eeee eeeee. Meeee eeee eeeeeeeee eee eeeeeeee eeeee eeeee, M8 eee eeeeeeeeee ee 88eee eee eee eeee eee eeeeeee ee 88°M eee eee eeee eeeeeeeee ee Meeeee 88. Mee eeee eee eeeeee ee 88°M; eeee M8(e) eee eeeeeeeee eeeeeeee. Meeee eeeeeee ee eee eeeeeee, 8M MMe (88eM) eee eeeee ee eee eeeeeee. Mee eeeeeee eeee eee eeeeee eeee MeMMe (88eM), eeeeeeee eeee Me8MM8 (8e), eee eeeeeeeee eeee MeMMe (8×88eM). Mee eeeeeeee eeeeeee eeeee eee eeeeee eeee eeeee eee eeeee (Me8MM8), eee eee eeeeeee eee eeee eeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/MeMM/Me8M 88:8:8) ee eeeeee eee eeee β-eeeee eeeee. Mee ee eee eeeeeeeeee ee MMMM (Meeeeeeee MM-M eeeeee).

References