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
1.2.1.3.5.2 Porta Radical-Type Strecker Reactions

DOI: 10.1055/sos-SD-210-00029

Ayaz, M.; De Moliner, F.; Morales, G. A.; Hulme, C.Science of Synthesis: Multicomponent Reactions, (20141115.

In contrast to the general nucleophilic addition of cyanide to imines resulting in the generation of α-aminonitriles, Porta and colleagues reported a metal-catalyzed free-radical reaction between in situ generated imines and formamide to produce α-amino amides 19.[‌93‌] Although the overall reaction yield is independent of the electronic properties of the aldehyde component, steric effects (i.e., bulky substituents) do have an impact (Scheme 19).

Meeeee 88 Meeeeeee(MMM) Meeeeeee Meeeeeee Meeeeeeeeee ee α-Meeee Meeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 Meeee (%) Mee
Me 8-MeMM8M8 88 [‌88‌]
eMe 8-MeMM8M8 88 [‌88‌]
e-Me 8-MeMM8M8 88 [‌88‌]
Me 8-MeMM8M8 88 [‌88‌]
8-MMM8M8 8-MeMM8M8 88 [‌88‌]
8-MMM8M8 8-MeMM8M8 88 [‌88‌]
8-MeM8M8 8-MeMM8M8 88 [‌88‌]
8-eeeee 8-MeMM8M8 88 [‌88‌]
Me 8-Mee 88 [‌88‌]
Me 8-MeM8M8 88 [‌88‌]

Mee eeeeeeeee ee eeee eeeeeeee eeeeeeeee eee “eeeeee” Meeeeeee eeeeeeee, eee ee eeeeee eeeeeeee eee ee eee eeeeee ee eee eeeeeeeeeeeee (Meeeee 88). Mee eeeeeee eeee ee e eeeeeeee(MMM) eee-eeeeeeee eeeeeeeee ee eeeeeeee eeeeeeee, eeeeeee ee e eeeeeeee eeeeeee eee ee eeeeeeee(MM), eeee ee eeeee eeeeeeeeeee ee eee eeeeeeeeee eeeee. Meeee eee eeeeeeee eeeeeee eeeeeeeee e eeeeee eeee eee eeeeeeeee, eeeeeee e eeeeeeeee eeeeeee, eee eeeeeeee(MM) eee eeeeeeeeeee eee eeeeeeee eeeeee ee eee eeeeeeee, eeeeeeee eeeee eeeeeeeee eee, eeeee e Meeee eeee, eeeeeeee eee eeeeeeeeeeeeeeee ee eee eeee-eeeeee eeeee ee eeeeeeeeeeee ee eee eeeeeeee. Meeeeee, eeeeeeeeeeee eeeeee ee eee eeeeeeeee eeeeeee eeeeeeeee ee eeeeeee eeeeeee, eeeee ee ee eeee eeeeeee eeeeeee ee eee eeeee eeeee eeeee ee eeeeeeee(MMM).

Meeeee 88 Meeeeeeee ee eee Meeee Meeeeee-Meee Meeeeeee Meeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

α-Meeee Meeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M8M8 (8 eeee, ee. 8.8 eM, 8.8 eeeee) eee eeeee eeeeeeee eeee e 88–88 eee eeeeee ee e eeeeeee eeee eeeeeeeeee ee eeeee (8 eeee, 8 eeeee), ee eeeeeeee (8 eeee, 8 eeeee), eee MeMe8 (8 eeee, 8 eeeee; ee. 8 eM ee e 88% eeeeeee eeeeee eeee) ee eeeeeeeee (88 eM). Mee eee ee eee eeeeeeee eee eeeeeeeee ee e eeeee eeeee eeeeee eeee eeee ee eeeeee. Me eeee eeeee, eee eeeeeeee eee eeeeeeee eeee M8M (8 eM) eee 88% ee MM8 eee eeeee eeeee eeeee eM eee eeeeeee. Mee eeeeeee eee eeee eeeeeeeee eeee MeMMe (8 × 88 eM), eee eeeeeeee eeeeeee eeeeee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeeee ee MMMe8 (88 eM). Mee MMMe8 eeee eee eeee eeeeee eeee M8M (8 × 8 eM) ee eeeeee eee eeeeeeee eeeeeeeee, eeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eee eeeeeeeee eeeeeee ee eeeeee eeeeeeeeeeeeee eeeeeeee α-eeeee eeeeee 88. Meee eeeeeeee eeeee ee eeeeeeee eeeeeeee ee e eeee eeeeeeeeeee eeee ee eeeeeeeeee eee eeeee eeeeeeeee ee e eeeeeeee eeeeeee.

References


Cookie-Einstellungen