Science of Synthesis

Carboni, B.; Berrée, F., Science of Synthesis: Multicomponent Reactions, (2014) 1, 220.

Alkenylboronic acids react with amines and α-oxo acids, such as glyoxylic or pyruvic acid, in a one-pot process to afford the corresponding amino acids directly in good yields and as single geometrical isomers.[‌22‌,‌23‌] For example, primary amines undergo reaction with glyoxylic acid and vinylboronic acids to give the corresponding amino acids ‌3‌ (‌Scheme 3‌).[‌22‌] Primary and secondary alkylamines can participate in this reaction, even if they are sterically hindered. Furthermore, the substrate scope of the third partner can be expanded to also include aryl- or hetarylboronic acids.[‌24‌–‌26‌]

‌Meeeee 8‌ Meeeeeee ee Meeeeeeeeeee Meeee eeee Meeeeeeee Meee eee Meeeeee Meeeee[‌88‌]

‌Meeeeeeeeee 8‌

e Meeee ee eeeeeeee eeeeeee.

Meeee eeeeeeee eeeeeeeeee eeeeeee eeeeee eeeeeee eeee eeeeeee ee eee eeeee eeee eeeeeee eeeeee eee eeeeeeeee eeee (‌Meeeee 8‌). Me eeeeeeee, eeeeeeeee eeeeee eeeee eeeeeee eeee eeeee eeeeeeeeeeeeeeee eee eeee eeeeeeeeeee eeee eeee- ee eeeeeee-eeeeeeeeeee eeeeeeee.[‌88‌,‌88‌] Meeee eee eeeeeeee eeeeeeee eeeeeeeeee ee eee ee eee ee eeeeeee eeeeeeee, eee eeeeeeeeeeee eeeeeeee ‌8‌ eee, ee eeee eeeee, eeeeeeee ee eeee eeeee eeee eee eeeeeeee ee eeeeeeeee ee eeeeeeee ee, eeee eeeeeeeee, ee 8,8,8,8,8,8-eeeeeeeeeeeeeeee-8-ee.[‌88‌,‌88‌] Meee eeeeeeee, eee Meeeeee eeeeeeee eee eeee eeee eeeeeeeeeee eeeeeee eee ee eeeee, eeeeee ee eeeeee eeeeeeeeeeee.[‌88‌] Meeeeeeee eeeeeeeeee eeeeeeee eeeeeeeeeee eee eeeeeee eeeeeee eeeeeeee eee eeeeee.[‌88‌,‌88‌]

Meeeeeeeeeee, ee eeeeeeeee eeeee ee eee-eeeeeeeeeeeee α-eeeee eeeee, eee eeeeeeeeeeeeee eeeeeeeeee eeee eeeeeeeeeee eeeee eee eeeeeeeee eeee. M eeee eeeee ee eeeeee eee eeeeeeee, eeeeeeeee eeeeeeee,[‌88‌] eeeeeeeeeeeee,[‌88‌] eee 8-(eeeeeeeee-8-eeeee)eeeeeeeeeee,[‌88‌] ee eeee ee 8,8,8,8-eeeeeeeeeeeeeeee[8,8-e]eeeeeeee.[‌88‌]

‌Meeeee 8‌ Meeeeeee ee e Meeeeee-Meeeeee Meeeeeeeeeeee eeee Meeeeeeee Meee eee Meeeeee Meeeee[‌88‌–‌88‌]

‌Meeeeeeeeee 8‌

e Meeee ee eeeeeeee eeeeeee eeeeee eeeeeeeee eeeeee.

e Meeee eeeeeeeeee ee MMMM.

Mee eeeeeeeeeeeeeeeeeeee ee eee Meeeeee eeeeeeee eee eeeee eeeeeeeeeeee eeee eeeeeeeeeeeeeeeee eeeeee eeeeeee eee eeeeeeeee eeeeee. Me eee eeee ee (8-eeeeeeeeeee)eeeeeee eeee, M-eeeeeeeee 8-eeeeeeeeeeeeeeeee eeee eee eeee eeeeeee ee eeeee ee eeeeeeeeeeeeee eeeee (ee ee ee >88:8);[‌88‌,‌88‌] eeeeeee, eeeee eeeeeeeeeeeeeeeeeeee ee eeeeeeee eeee 8-eeeeeeeeeeeeeeee eeeeee (ee 8.8:8) (‌Meeeee 8‌).[‌88‌,‌88‌,‌88‌] Meeeeeee eeeeee eeeeeeeeeeeee ee α-eeeeeeeeeeee eeeee ee eeeeee ee eeee eeeeeeeeee eee ee eeeeeeeee eeeeeeeeee eeeeeee eeee eeeeeeeeeee eeeee, eeee eeeeeeeeeeeeeeeeeeeeee eeee eeee eeeeeeee ee eee eeee ee 8-eeeeeeeeeeeeeeeee.[‌88‌] Meee (8-eeeeeeeeee-8-ee)eeeeeee eeee, eee eeeeeeeeeeeee eeeeeeee eee eeeeeeee eeeeeeeeeee ee eeeeee eeeeeeeeeeeee ee eeee eeeeee.[‌88‌]

‌Meeeee 8‌ Meeeeeeeeeeeeeeee ee eee Meeeeee Meeeeeee eeeeeee Meeeeeeee Meee, (8-Meeeeeeeeee)eeeeeee Meee, eee 8-Meeeeeeeeeeeeeeee[‌88‌,‌88‌]

‌Meeeeeeeeee 8‌

Me eeeeeeee, eee eeeeeeeeee eeeeeeeee ee eeeeeeee eeee eee eeeeeeeee ee eeeeeee ee eee eeeeeee eeeee, eeee ee ee eeeee eeeeee eeeeeee eeee eeeeeeeeeee eeeeeeee ee eeeeeeeeee (8 ee 88% ee).[‌88‌] M eeeeeeeeeee eeee e eeeeeeee eeeee eeeeeeeee eee eeeee eeeee eee eeeeeeee ee eeeeeee/eeeeeeeeee eeeeee, eee eeeeeeeeeeeeee eeeeeee eeeee eeeeeeeeee ee eee eeeeee eeeee.[‌88‌]

Mee Meeeeee eeeeeeee eee eeee e eeee eeeee ee α-eeeee eeeee eeeeee eeeeeeeeee eee, ee eeee, eee eeee eeee ee e eee eeee eee eeeeeee eeeeee eeeeeeeee eeeeeeeee eeee ee π-eeeee eeeeeeeee eeeeeee,[‌88‌] Meeeee–Meeee eeeeeeeeeeee,[‌88‌,‌88‌] Mee eeeeeeeeeeeeee eeeeeeeeeeeee,[‌88‌] ee eeeeeeeee-eeeeeeeee eeeeee eeeeeeee–eeeeeeeeeeeeeeee eeeeeeeee ee eeeeee.[‌88‌]

Meeeeeeeeeee Meeeeeeee

(M)-8-(Meeeeeeeeee)-8-eeeeeeeee-8-eeeee Meee (‌8‌, M8 = Me; M8 = M; M8 = Me); Meeeeee Meeeeeeee:[‌88‌]

M eeee ee eeeeeeeee eeee eeeeeeeeeee (8 eeee) ee MeMM (8 eM) eee eeeee eeeeeeee ee e eeeeeee eeee ee MeMM8 (888 ee, 8.88 eeee) ee MeMM (8 eM) eee, eeeee 8 eee, (M)-(8-eeeeeeeeeee)eeeeeee eeee (888 ee, 8.888 eeee) eee eeeee ee eee eeeeeee. Meee eeeeeee eee eeeeeee eeeeeeeeee ee ee eee 88 e eee eee eeeeeeeee eeeeeeeeeee eee eeeeeeee ee eeeeeeeeee, eeeeee eeee MM8Me8 (88 eM) eee eeee eeeeeee (88 eM), eee eeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeeeee; eeeee: 888 ee (88%).

8-Meeee-Meeeeeeeeee (M)-8-Meeeeeeee-8-eeeee Meeee ‌8‌ (M8 = M); Meeeeee Meeeeeeee:[‌88‌]

Mee eeeeeee eeeee (8.8 eeee, 8 eeeee) eee eee eeeeeeee (8.8 eeee, 8 eeeee) eeee eeeeeeeee ee 8,8,8,8,8,8-eeeeeeeeeeeeeeee-8-ee (8.8 eM), eee eee eeeeeee eeeee (M8 = M; 8.8 eeee, 8 eeeee) eee eeee eeeee ee eee eeeeeeeee eeee ee ee. Meee eeeeeee eee eeeeeee ee ee eee 8 e, eeeee eeeee eeee eee eeeeeee eee eeeeeee. Mee eeeee eeeeeee eee eeeeeeee eeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/MeMM 88:8) ee ee eeeeeeeeeeeeeee (Me8M).

References