Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
41.1.1.5.54 Method 54: Addition to a Nitroalkene Using a Carbanion Prepared from a 1,3-Diester

DOI: 10.1055/sos-SD-041-00002

Aitken, R. A.; Aitken, K. M.Science of Synthesis, (201041184.

In Scheme 201 (Section 41.1.1.5.19) is shown a reaction of a malonate with a nitroalkene in a tandem cyclization reaction. Deprotonated malonate esters have been useful reagents in many kinds of nucleophilic reactions, and have also been used extensively in Michael additions to nitroalkenes. Examples are shown in Schemes 257 and 258.

Meeeee 888 Meeeeeee ee Meeeeeee Meeeee ee Meeeeeeeeeee[‌888‌,‌888‌,‌888‌‌888‌]

Meeeeeeeeee 888

M8 M8 M8 M8 M8 Meeeeeeeeee Meeeee (M/M)e Meeeeeeeee Meeeee (%) Mee
Meeeeeeeeeeee ee Meeeeeee Meeeeeee Meeeeeee
Me M 8-MeMM8M8 M M e.e. eee eeeeeeee eeeeee ee eeee MeMMe/MeMM eeee eeeeeeee ee eeeeeeeeeee (eeeeeeeeee), eeee ee MeMM, M8M 88 [‌888‌]
Me M Me M Me e.e. eee eeeeeeee eeeeee ee eeee eeeeeeeeee ee Me ee eeee eeeeeee eeee eeeeeeee ee eeeeeeeeeee, eeee MeMM, M8M e.e. [‌888‌]
Me Me M M M eeee MeMMe/MeMM, eeeeeee-8,8,8-eeeee eeeeeeee ee eeeeeeeeeee eeee 8e, 88°M ee ee, 8e, eeee MeMM, M8M 88 [‌888‌]
Me M MMMe M M e.e. eeeeeeee ee eeeeeeee ee MeMMe/MeMM, ee eeeeeeee ee eeeeeeeeeee eeee 88eee, 88°M, 8e, eeee ee, eeee ee MMe e.e. [‌888‌]
Me M Me Me M e.e. MeMMe, MeMM eeeeeeee eeeeeeee ee eeeeeeeeeee, 88°M ee ee, 8e, eeee ee MeMM 88 [‌888‌]
Me M M M e.e. Me, MeMM eeee eeeeeeee ee eeeeeeee eeeee eeeeeeeeeeeee, eeee, 8.8e, eeee MeMM, eee 88e [‌888‌]
Me M Me Me M M MeM, MMM, 8°M, 88eee MMM, 8°M, 88eee, eeee ee MeMM 88 [‌888‌]
Me Me Me Me M M MeM, MMM, 8°M, 88eee MMM, 8°M, 88eee, eeee ee MeMM 88 [‌888‌]
Me MM8MM=MMe8 Me M M M MeM, MMM, 8°M, 88eee 88°M, 8e, eeee eM 8 eeeeeeeee eeeeee 88 [‌888‌]
Me M (MM8)8MM8 M M M Me, MeMM, 88°M eee eeeeeeeeeee eeee 8.8e, <88°M, eeee ee, 8.8e, eeee M8M, ee MMe 88 [‌888‌]
Me M MM8 M M M MeM, MMM, ee, 8e eeeeeeee eeeeeeee ee eeeeeeeeeee, eeee ee, 88e, eeee ee MM8Me 88 [‌888‌]

e e.e.=eee eeeeeeee.

e Meeee eeee eee eeeee; eeeeeee eee eeeeeeeeeee eeeeeeeeeeee.

Meeeee 888 Meeeeeeeeeeeeee ee Meeeeeee Meeeee[‌888‌,‌888‌]

Meee eeeeeeee, eeeee eeeeeeeee eee eeeeeeeeeeeeeee eeee eeee ee eeeeeeee ee eeeeeeeeeeeee eeeeeeeee eeee eeeeeeeeeeee ee eeee eeeee eee ee ee eeeeeeeeeeeeeeee eeeeee. Meeeeeee eeeee eeeeeeeee 888888 eee eeeee ee Meeeeee 888 eee 888.

Meeeee 888 Meeeeeeee Meeeeeeeeeeeeee Meeeeeee ee Meeeeeeee ee Meeeeeeeeeee[‌888‌‌888‌]

Meeeeeeeeee 888

M8 M8 M8 Meeeeeee (eee%) Meeeeeeeee Meeee Meeeeeeeee ee (%) Meeee (%) Mee
Me M Me 888 (888) MMM, 8°M ee ee, 8e 888M 88 88 [‌888‌]
Me M Me 888 (88) MMM, 88°M, 88e 888M 88 88 [‌888‌]
Me M Me 888 (8) eeeeeee, 88°M, 88e 888M 88 88 [‌888‌]
Me M Me 888 (8) eeeeeee, 88°M, 88e 888M 88 88 [‌888‌]
Me M Me 888 (88) MM8Me8, 88°M, 88e 888M 88 88 [‌888‌]
Me M Me 888 (88) eeeeeee, 88°M, 88e 888M 88 88 [‌888‌]
Me M 8-Mee 888 (88) eeeeeee, 88°M, 8eee 88 [‌888‌]
Me M Me 888 (88) e-eeeeee, ee, 88e 888M 88 88 [‌888‌]
Me Me Me 888 (88) e-eeeeee, ee, 888e 888M 88 88 [‌888‌]
Me M eeee 888 (88) MMMe8, ee 888M 8888 8888 [‌888‌]
Me M Me 888 (88) eeeeeee, 88°M 88 88 [‌888‌]
Me Me Me 888 (8.8), Me(MMe)8 (8), 8-eeeeeeeeeeeeeeee (8.8) MMMe8, ee, 88e 888M 88 88 [‌888‌]

Meeee e eeeeeeeee eeeeeee ee eeeeee 888 ee eeeeeeee, eeeeeee 8-eeeeeeeeeee eeeeeeeee (M8=Me, Me; M8=Me, M, Me, MM8MM=MM8, MMMee, MMMe, MMe) eeee eeee eeeee ee (M)-8-eeeee-8-eeeeeeeeeeee, eeeeee eee eeeeeeee eeeeeeee ee 8888% eeeee eee 8888% eeeeeeeeeeee eeeeee. Mee eeeeeeee ee eeeeeee 8-eeeeeeeeeeeeee ee eeeee ee Meeeee 888.[‌888‌]

Meeeee 888 Meeeeeeee Meeeeeee ee Meeeeee 8-Meeeeeeeeeeeee ee e Meeeeeeeeee[‌888‌]

Meeeeeeeeeeeeee eeeeeeee ee eeeeeeeee ee eeeeeeeeeeee eee eeee eeee eeeeeeee (Meeeee 888).[‌888‌,‌888‌]

Meeeee 888 Meeeeeeeeeeeeee Meeeeeee ee Meeeeee Meeeeeee ee e Meeeeeeeeee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeee 8-(8-Meeeeeeeee)eeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

Me (8.88e, 88eeee) eee eeeeeeeee ee MeMM (888eM) eee eee eeeeeee eee eeeeee, eeeee eeeeeeee eeeeeeee (888; 88eM, 88.88e, 888eeee) eee eeeee. M eeeee eeeeee ee eeeeeee-8,8,8-eeeee eee eeeee eee eee eeeeeee eee eeeeee ee 88°M. Meeeeeeeeee eeee eeeeeeeeeee, eeeeeeeeeee (888; 8.8eM, 8.88e, 88eeee) eee eeeee eeee eeeeeeee eeee 8e. Mee eeeeeee eee eeeeeee ee 88°M eee 8e eee eeee eeeeeee ee eeee ee ee eeee 8e. Mee eeeeeee eee eeeeee ee 8°M eee eee MMe(e) eee eeeeee eeeeeee eeeee eee eeeeeee eee eeeeee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeee ee ee eeeeeee eee eeeeeeee ee eeeeee eee eeeeeeeee MeMe. Mee eeeeeeee eee eeeeeeeee ee eeee 888; eeeee: 8.8e (88%); ee 888°M/8.8Meee.

Meeeeee 8-(8-Meeeee-8-eeeee-8-eeeeeeeee-8-ee)eeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeeeeee ee MeM (88ee, 8.8eeee) ee MMM (8eM) ee 8°M eee eeeee eeeeeee eeeeeeee (888; 888ee, 8.888eeee), eeeeeeee ee eeeeeeeeeee 888 (888ee, 8eeee). MMM eeeeeeee eeeeee eeee eee eeeeeeee eee eeeeeeee eeeeee eeeeeeeeeee. Mee eeeeeee eee eeeeee eeee 8% ee MeMM eee eeeeeeeee eeee MM8Me8 (8×88eM). Mee eeeeeeee eeee eeeeee eeee M8M (88eM), eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee ee eeee 888; eeeee: 888ee (88%); 8M MMM (MMMe8, δ): 8.88 (e, 8M, M=88.8Me), 8.88 (e, 8M, M=88.8Me), 8.888.88 (e, 8M), 8.88 (e, 8M), 8.88 (ee, 8M, M=88.8, 8.8Me), 8.88 (ee, 8M, M=88.8, 8.8Me), 8.88 (e, 8M), 8.88 (e, 8M, M=8.8Me), 8.88 (e, 8M, M=8.8Me 8.88 (e, 8M, M=8.8Me).

Meeeeee (M)-8-Meeeee-8-(8-eeeee-8-eeeeeeeeeee)eeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee Me(MMe)8 (88.88ee, 8.888eeee), eee eeeeee eeeeee 888 (88.88ee, 8.888eeee), eee MMMe8 (8.8eM) eee eeeeeee eee 88eee, eeeee eeeee M8M (8.8 μM) eee eeeee. Mee eeeeeeeee eeeeeee eee eeeeeee eee 8e, eeeee eeeee MMMe8 (8.8eM) eee eeeeeeee 8-Å eeeeeeeee eeeeee (888.8ee) eeee eeeee ee eee eeeeeee, eee eeeeeeee eee eeeeeeeee eee e eeeeeee ee 8e. Mee M8M eeeeeee eee eeee eeeeeeeeee ee Meee Meeeeee eeeeeeeee. Me eee M8M eeeeeee eee >88eee, eeeeeeee eee eeeeeeeee eee eeeeeeeeee eeeeeeeee eeeeee eeee eeeee. Meee eee M8M eeeeeee eee <88eee, M8(e) eee eeeeeee eeeeeee eee eeeeeee eee e eeeeeee ee 8eee eee (M)-8-eeeee-8-eeeeeeeeeeee (8.88e, 8.88eeee) eee eeeee ee e eeeee eeee 8eee. MMMe8 (8eM) eee eeeee ee e eeeee, eeeeeeee ee eee eeeeeeee ee eeeeeee eeeeeeeeeeeeee (8.88e, 88.88eeee) eeee 8eee eee eeeeeee. 8-Meeeeeeeeeeeeeee (88.8 μM, 88.8ee, 8.888eeee) eee eeeee eeeeeee eee eeeee, eeeee eeeee M8 eee eeeeeee eeeeeee eee eeeeeee eee e eeeeeee ee 8eee. Mee eeeeeee eee eeeeeee eeeee M8 ee ee eee 88e. Meeee eeee eeee, MMMM eeeeeeee eeeeee eeeeeeeeee, eee M8M (8eM) eee eeeee ee eeeeee eee eeeeeeee. Mee eeeeeee eee eeeeeee ee eeee eee ee eeeee 8eee ee eeeee eee eeeeee ee eeeee. Meee, eee eeeeeee eee eeeeeeee eeeeeee e eee ee Meeeee. Mee eeeeee ee eee eeeeeeee eeee eeeeeeeee, eee eee eeeeeee eeeee eee eeeeee eeee eeeee (88eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeeeee e eeeeee eee. Mee eee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 8:8) ee eeee 888 ee e eeeee; eeeee: 8.88e (88%); >88% ee; Me 8.88 (MeMMe/eeeeee 8:8); ee 8888°M; 8M MMM (MMMe8, δ): 8.888.88 (e, 8M), 8.88 (ee, 8M, M=88.8, 8.8Me), 8.88 (ee, 8M, M=88.8, 88.8Me), 8.88 (ee, 8M, M=88.8, 8.8Me), 8.888.88 (e, 8M), 8.888.88 (e, 8M), 8.88 (e, 8M, M=8.8Me), 8.88 (e, 8M, M=8.8Me).

References


Cookie-Einstellungen