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
1.1.3 Enamine Catalysis of Mannich Reactions

DOI: 10.1055/sos-SD-204-00021

Benohoud, M.; Hayashi, Y.Science of Synthesis: Asymmetric Organocatalysis, (2012173.

General Introduction

Asymmetric reactions catalyzed by amines involving enamine intermediates were developed after the discovery of the intermolecular proline-catalyzed aldol reaction in 2000.[‌1‌] In the same year its application was reported for the aza variant of the aldol reaction: the Mannich reaction.[‌2‌]

Me eee eeeee-eeeeeeeee Meeeeee eeeeeeee, eee eeeeeeee ee eeeeee 8 eee eee eeeeee eeeee 8 eeeee eeee ee eeeeeee (eeeee) 8, eeeee eeee eeeeee eeeeeee eeee ee eeeee (eeeeeeee) 8. Mee eeeeeeeee eeeee ee eeeeeeeee ee eee eeeeeeeeeeee ee eee eeeeee eeeee eeeee eeeeeeeeee ee eeeeeeeeeeee 8. Mee eeeee eeeeeee ee e β-eeeee eeeeeeee eeeeeeee 8. Mee eeeee eeeeeeee 8 eee ee eeeeeeeee (eee-eeeeeeeee Meeeeee eeeeeeee) ee ee eee ee eeeeee ee eeee ee eee eee ee eee eeeee eee eeeeeeee eeeeeeeeee eeeeeeee (eeeee-eeeeeeeee Meeeeee eeeeeeee) (Meeeee 8). Mee eeeeeeee ee eee eeeeeeee ee eeeeeeeee eee eeeeeeee ee eee eeeeeeeeee. Meeee eeeeeeeee eeeee eee eeeeeeeeee ee eeeeeeeeee β-eeeee eeeeeeee eeeeeeeee.

Meeeee 8 Meeeeeee Meeeeeeee ee eee Meeeeee Meeeeeee

Meee eeeeeeeee eeeeeeee eeeeeeeee eee eeee eeeeeeeeee ee eeeeeee eeeeeeee eeeeee ee eeeee ee eeeeeeeeee eee eeeeeee eeeeeee ee eeeeeee ee ee eeee eeeeeeeee ee eeeeeeee ee eeee eeeeeeeeeeeeee,[‌8‌] eee eeee ee eeeeeeeeeee eee eeeeeeeeeee ee eeeeeeeeee eeeeeeeeeeeeeeeeeee eeeeee eeeee.[‌8‌‌8‌] Meeeee, eee eeeeee β-eeeee eeeeeeee eeeeeee ee eee Meeeeee eeeeeeee eee eeee eee ee eeeeeeeeee eeeeeeee. Mee eeeee eeeeeee ee ee eeeeeeeeeeeeeeee eeeeeeeeeeeeeeeeeee Meeeeee eeeeeeee eee eeeeeeee ee 8888.[‌8‌]

Meeeeee eee eeeeeeee eeeeeeeeeee eeee eee eeeee eeeee eeeeeeeee eeee eee eee eeeeeeeeee Meeeeee eeeeeeee. Mee eeeeeeeee ee eee eeeee, ee eeee ee ee eee eeeeeeeeeeeee eeeeeee, eee e eeeeeee eeeeeeeee ee eeeee eeeeeeeeeeee eeeeeeeeee. Meeeeeeeeeee eeee eeeeeee eeee eeeeeeee eeee eeeeeeee eeeeeeeee eeee ee eeeeeeeeeee.[‌8‌] Meeeeeee, eeeeeeee eeeeeee eeee eeeeeeeeeeee eee eeee eeeee eeee eeeeeeeeeeee eeee eeeee eeeeeee eeee eee-eeeeeeee eeee eeeeee.[‌88‌] Meeeeee eeeeee eee eeeee eeeee eeee eeee eeee eeeeeee eee eeeeeeee ee eeeeeeeee eee eeee eeeeeeeeeeeeee.

Mee eeeeeeeeeeeeee eeeeeee ee eee Meeeeee eeeeeeee eeeeeee (8) ee eee eeeeeeee, (8) ee eee eeeeeeee ee eee eeeeeee, eee eeee (8) ee eee eeeee eeeeeeee.

(8) Meeeeeeeeeeeeee eeee ee Meeeeee eeeeeeeee eee ee eeeeeee eeee eee eeeeee: eee eeeee eeeeeeee eeeeeeeee eeee ee eeee/eeeeeeee eeee eeeee, ee eeeeee eee eeeeeeee ee eee eeeeeeeeeeee, eee eee eeeee eeeee eeeeeeee eeeeeeeee eeee e eeeee, eeeeeeeee eeeee, eeee ee eeeeee eee eeeeeee eee eeeee eee eeeeeeee ee eee eeeeeeeeeeee eeee eee eeee (Meeeee 8).

Meeeee 8 Meeee-Meeeeeee Meeeeee ee eee Meeeeeeeeee

(8) Meeeeeeeeeeeeee eeee e eeeeeeeeeee eeeeeeee eeee eeee eeee eeeeeeeeeeee.[‌88‌] Meeeeeeeeee eeeeeee ee eee eeeeeee eeeeeeeee (eeeee eeeeeeeeee eee eeeeeee eee eeeeeeeee) eeeeeee eeee eeeeee eeeeeeeee eeeee eee eeeeeeeeee eeeeeeee.[‌88‌] Meee eeeeeee ee eee eeeeeeeeeeeee eeeeeee eeeeee, eeee eeeeeeeee eeeeeeeeee eee ee eeeeeee. Mee eeeeeeeeeeeeee ee eee eeeeee eeee ee eee eeeeeee eee eeeeeeee: M ee M, eee eee eeeeee eeee eee ee eee ee eeee eeeeeeee ee eee eeeeeeeeeee ee eee eeeeeeeeeee (Meeeee 8). Meeeeeeeeeeee eeeeeee ee eee eeeeeee eeeeee eeee e eeeeeeeeeeeeee eeeee eeeee eee ee eeeeeeeee eeeeeeee eeeeeee eeee Meeee- eee Meee-eeeeeeee eee eeeeeee eeee Meeee- eee Meee-eeeeeeee. Meeee eeeeeeee eee eeeeeeeeee eeee eee eeeeeee ee M-eee eeeeeeee ee eeeee eeeeeeeeee.[‌88‌] Meee eeeeeeee, eee eeeeeee eeeeeeeee eee eeee eeeeeeee ee MMM eeeeeeeeeeee ee eee eeee ee eeeeeee,[‌88‌] eeeeeeee eeeeeeeeeee, eee eeeeeeee eeeee eeeeeeeeeee.[‌88‌] Mee eee eeeeeee eeeeee eeee eeeeeee ee eeeeeeee eeeeeeeee eeee eee Meeee-eeeeeee eee eeee eeeeeeee. Meee eeeeeeeeeeee ee eeeeeeee ee ee eeeeee eee ee eeeeeeeeeeeee eee eee eeeeeeee eeee eee eeeeeeeeeeeee eeeeeee eee. Me eee eeee ee eeeeeeee eeee eeeeeeee eeeeeeeeeee eee eeeeeeee eeeee eeeeeeeeeee, 88 eeeeeeeee eeeeeeeeeeeee eeeeeeeeeeee ee eeeeeee eeeeeeee eeee eeee eeeeeeee. Me eee eeeee, eee eeeee eeeeeeeeee eee M-eeeeeeee. Me eee eeee ee eeeeeeee eeeee eeeeeeee eeee eeeee eeeeeeee eeeee eeeeee, M-eeeeeeee eeee eeee eeee eeeeeeee ee eeeeeeee ee M-eeeeeeee.

Meeeee 8 Meeeeeee Meeeeee Meeeeeeeee

(8) Meee eeeeeee ee eeeeee, eee eeeeeeeee eeee eeeeeeeee eeeeeeeeee ee eeeee eeee M-eeee-eeeeeeeeee eeeeee. Me eee eeee ee eee eeeeeee-eeeeeeeee eeeeeeee ee e eeeeeeee eeeeeeee eee ee M-eeee-eeeeeeeee eeeee, eee eeeeeeeeeeeeee eeeeeeeee eeeeeee eee M-eeeeeeeeee eeeee eee eee eeeeeee eeeeee, ee eeeeeeeeeee eeee eeeeeeee-eeeeeee eeeeeeeeee ee eee eeeee ee eee eeee eeeeeeeeeeeee ee eeeeeee, eeeeeee e Me-eeee eeeeee ee eee M-eeeee ee eee Me eeee ee eee Meeee-eeeeeee. Mee eee-Meeeeee eeeeee ee eeeeeeee eeeeeeeeeee, ee eeeeeeee eeee eee eeeee-eeeeeeeee eeeee eeeeeeee, eeeee eee eeee-eeeeeee ee eeeeee eeeeeeeeeee (Meeeee 8).[‌88‌,‌88‌]

Meeeee 8 Meeeeeeeee-Meeee Meeee eee eee eee-Meeeeeeee Meeeeee-Meeeeeeee Meeeeee Meeeeeee eeee M-Meeeeeeeee[‌88‌,‌88‌]

Mee eeee-Meeeeee eeeeeee eee eeee ee eeeeeeee eeee eeeee eeeeeeee eeeee eeeeeeeee eeee eeeeee eeee eeeeeeeeeee eeeeeeeeee, eeee e eeeeeeeee M eeeeeeeeeeeee ee eee eeeeee eeee ee eee eeeeeee (eee Meeeeee

M-(8-Meeeeeeeeeeee)-eeeeeeeee eeeeee eeee eeeeeeeee ee eee eeeee ee eeeeeeeeeeeeeee Meeeeee eeeeeeeee. Meeeeee, eeee eeeeee eeeeeeeeeeee eeee eeeeeeee eee eeeee ee eee eeeee eeeeeeeee ee M-(eeeeeeeeeeeeee)- eee M-eeeeeeee-eeeeeeeee eeeeee. Meee eeeee eeeeee eee eeeeeeeee ee eee eeeeeeee (eeee ee eeeeeee eeeeeeee-eeee eeeee), eee eeeeeeeeeeeeeeeee ee eee eeeeeeee eee ee eeeeeee eee eeee-eeeeeeeee eeeeeeeee eee eeeeeeee (eee Meeeeee M-Meeee-eeeeeeeee eeeeee, eeeeee eeeeee, eee eeeeeeeee eeee eeee eeee eeeeeeeeeeee ee eeeeeeeeeeeee. Mee Meeeeee eeeeeeee eeeeeeee eeee eeeeeeeeee eeeeeeeeeeeeeeeeeee eee eee eeeeeeeeeeeee eeeeeeeeeee eeeeeeee eeeeee ee eeeeeee eeeeeeeeee eeeeeeeeeeeee (eee Meeeeee

Mee eeeeeeeeee Meeeeee eeeeeeee eeeeeeeee ee eeeeee eee eeee eee eeeeeee ee eeeeeeee eeeeeee[‌88‌‌88‌] eee eee eeeeeee eeee ee ee eeeeeeeee eeee eeeeeeee eeeeeeeee eeeeeeeeee.