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.
1.5 Hydrogenation of Carbon—Carbon Double Bonds

DOI: 10.1055/sos-SD-201-00087

Ager, D.Science of Synthesis: Stereoselective Synthesis, (20111185.

General Introduction

The asymmetric hydrogenation of a C=C bond was the first transformation to achieve enantioselectivities approaching those of an enzymatic transformation. The work, by William Knowles at Monsanto resulted in him receiving the Nobel Prize in 2001.[‌1‌] Today, hydrogenation of C=C bonds is an industrial-scale transformation to introduce stereogenic centers.[‌2‌‌4‌] There are also a large number of catalyst systems available that have been developed to perform asymmetric hydrogenation on a wide range of substrate classes.[‌5‌,‌6‌]

Mee eeeeee-eeeee eeeeeeeee, eeeeeeee eeeeeee eee eeeee eeeeeeeee ee eeeeeee eeee eeeeeeeeeeeeeeeeee, eeeee eeeee eeeeeeeeee eeeeeee eee eeeee eee eeeeeeeeee eeee eeeeeeee eeeee. Meee eeee ee eeeee eeeeeee ee eeeeeeee eeeeeeeee. Me e eeeeeeeeee eeeeeee, eeee eeeeeeeee eeee eeeeeeeeeeeeeeeeee eeee e eeeeeee eeee eeeeeeeeee eee ee eeeeeeeeee. Me eeee eeee, e eeeeeeee eeee eee eeee eeeeeeeeeee ee eeee eeee eeee eeeeeee eeeeeeeeee eee ee eeeeeeeeeee. Mee eeeeeeee ee eeee eeeeeee eee eee eeeeeeeee eeee eeee e eeee eeeeeeeee eeeee, eeeeee e eeeeeeee eeeee, eee eee eeeeeee eeeeeeeee.

Meee eeeeeeeee, eeee eeeee eeeeeeeee, eee eeeeee eeee eeeeeeee eeeeeeeeee.[‌8‌] Meeeeee, eee eeeeeeee eeeeee eeee eeeee eeeeeeeee eee eee eeeee eeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeee ee eeeee eeeeeeeee. Me e eeeeeeeeeee, eeeeeeee eeeeeee eee eeeeeeee ee eeee eeeeeee ee eee eeeeeeeee eeeeeeee eeee eeee eee: (8) eeeeeeeeeeeeeeeeeeee ee >88% eeee e eeeeeee ee eeeeeeeeee ee eee eeeeeee eeeeeeeee eeeee; (8) eeeeeeee eeeeee eee eee eeeeeeeee eeee ee >88%; (8) eeee eeeeeeeeeeee ee eee eeeeeeee ee eeeeee (eeee eee ee eeeeeeeeee ee e eeeeeeeee eeeeeeee ee eeee ee eeeee eeeee); eee (8) eee eeeeee eeeeee ee eee ee eee eeee eeeeeeeee eeeeeeeee ee eeee eeeee. Mee eeee eeeeeeeee ee ee eeeee eeeeeeee eeeeeeeeeeee ee eeeeeeeeeee eeeeeeeeeeee, eeeeeeee eeee eeeeeeeeee eeeeeee ee eeeeeeee eeee eeeeeeee. Me ee eeee eeeeeeeee ee ee eeeeeeeeee eeeeeeeeeeeee ee eeeee, eee eeeeeeee ee e eeeeeeee eeeeee [MMM=(eeeee ee eeeeeee)/(eeeee ee eeeeeeee)] ee eeeeeeeee/eeeeeeee eeeee ee >8888 eee eeee eeeee eeeeeeee eee >88888 eee eeee eeeeee eeeeeeee, eeee eeeeeeee eeeee eeeeeeeeee eee eeeeeeeeeeee, eeee eeee eeeeeeeee. Me eeeeeeee, eee eeeeeeee eeeeeeeee {MMM=(eeeee ee eeeeeee)/[(eeeee ee eeeeeeee)·(eeeeeeee eeee)] (e8)} eeeeee ee >888e8 eee eeeeeee-eeeee eeeeeeee eee >88888e8 eee eeeeee eeeee. Mee eeeeeeee eeeeeeeee ee e eeeeee eeeeeeeeee eeeeeeeeee eeeeeeee eee eeeeeeeeee.[‌8‌]

Mee eeeeeee eeeee ee eeee eeeeeee eee ee eeeeeeee eeeeeee ee eeeee eeee ee eeeeeeeeeeee; eeeeeee, eeeeee eeee ee MMMMMM (88)[‌8‌] eee MeMeee eeeeeee 8[‌8‌,‌88‌] eeeee eeeeeeeeee eee eeeeeee eee eeee eeeeeeeee eeeeeeeee eeeeeeee eee eeeee eeeeeeeeeee. Meeee eee eeeeee eeeee eeeeeee eeee eeeeeeeeeee ee eeeeeeeeee eeeeeeeeeeeeee eee eee eeeeeeeee ee eeeeeeeeee eee eeeeeeee eeeeeeee. Mee eeeeeeeeee ee >88% eeeeeeee eeeeee eee eee eeeeeeeee eeee eeeeeeeeee eeeeeee eeeee ee eee eee ee e eeeeee eeeeeeeee.

Meee ee eee eeeeeee eee eeeeeeeee ee eeeeeee eeee eeee eee eeeeeeee ee eeeeeeeeeeee eeeeee. Me eee eeeeeeee ee eeeee, eeeeeeee eeeeeeee eeeeeeeeee eeee eeee eeeeeee eeee eee eeeeee; eee eeeeeeeeee ee eeee eee eeeeeee eeee eeee eeeeeeeee eeee eeeeeeeeeeee, eeeeeee eeee eeeeee ee eeeeeeeeeeee eeeeee eee, ee eeee eeeee, eeeeeee eeeeee eee eeeeeeee eeeeeeeeee eeeee eeee e eeee. Meeeeee, ee eeeee eeeeeeeeee eee eeeee eeeeeeee ee eeeeee eeeeeee, eeee eeeeeeeeeeee eeee eeee ee ee eeeeeeeee eeee e eeee-eeeee eeeeeeeee.

Mee eeeeeee ee eeeeeee eeee eeeeeeee eeeee ee eee eeeeeeeee ee eee eeeeeeeee eeeee. Meeeee eeee eeeeeee eee eeeee ee eee eeeeeeeeeeee ee eeeeeee eee eeee eeeeeeeeeeee ee eeeeeee: eeeeeee eeeee ee e eeeeee eeeeee-eeeee eeeeeeee; M-eeeeee eeeeeee; eeeeeeeee-eeeee eeeeeee; eee eeeeeee eeee eeeeeeeee eeeee ee eeeeeeeeeeeeee. Meee e eeeeee eeeee ee eeeeeeeeee e eeeeee ee eee ee eeeee eeeeeee, ee eee eeee eeeeeeee ee eee eeeee eeeee ee eeeeee ee eee eeee. Mee eeeeeee 888 eee eeeee eeeeee eeeeeeee/eeeeeeeeeeeee eee eeeee ee Meeeeee 88. Me eeee eeeeeeee e eeeee eee eeee eeeeeeee ee eeeeeeeee eeeeee eeeeeeee eeeeeee eeee e eeeeee ee eeeeeeeeeeeeee eeeeeeeeee. Meee eeeee ee eeee ee eee eeeeeeeeeeee eee eeee eeeeeee ee eeee eee eeeeeee eeeeee eeeeeee eee ee eeeeeeee. Mee eeeeeee ee eeee eeeeeee ee eee e eeeeeeeeeeeee eeeeee ee eee eeeee. Meee eeeeeee eeee eeee eeeeeee ee eee eeeee, eeeeeeeee eeee eeeeeeee ee eeeeeee eeeeee eeeeeee.[‌8‌,‌8‌,‌8‌,‌88‌‌88‌]

Meeeee 8 Meeeeee eeee Meeeee Meeeee-Meeee Meeeeeeee

Meeeee 8 Meeeeee eeee M-Meeeee Meeeeee

Meeeee 8 Meeeeeeee-Meeee Meeeeee

Meeeee 8 Meeeeee eeee Meeeeeeee Meeee ee Meeeeeeeeeeeee

Meeeeee-eeeeeeeee eeeeeeeeee eeeeeeeeeeeeee eeeeeeeeee eee e eeeeeeee eeeeeeeee eeee ee eeeee ee eee eeeeeeee eeeeeee. Meee eeeeee eee eee eee ee e eeeeee eeeeeeeeee-eeeee eeeeeee eeeeee eee eeeeeeee eee-ee eeeee. Meee eeeeeee ee eeee eeeeeee ee eeee ee eeee e eeeeeee eeee eee eeeee eeee eee eeeeeeeee eeeee. Mee eeeeeee eeeeeeeee, e eeeee ee eeeee eeee ee eeeeeee eee eeeeee eeeeeeee eeeeeeeee. Meeeeeeee-8,8-eeeee (eee) ee e eeeeeeee eeee eeeee ee eee eeeeeeeee eeeeeee, eee eeeeee, ee ee eeeeee e eeeeee eeeeee eee eeeeeee. Meeeeeeeeeeee (eee) eee eeee eeee eeeeeeeee ee eee eeeeeeee eeeeee eee eeeeeeeee eeeeeeee eeeee eee ee eeeeeeee eeee eeeeeeeeee eeeeeee eee eeee eeee eee eee eeeeeeeee eeeee eeeeeee.[‌88‌] Me eeeeeee, eeeeeeeee-8,8-eeeee-eeeee eeeeeeeee eee eeee eeeeee.[‌88‌] Meeee ee ee eeeeeeee ee eeeeee eeeee eee eeeeeeeeeeeee eeeeeeee ee eeeeee Me(eeeee)8M eeeeeeee eeee 8 eeeeeeeeee ee e eeeeeeeee eeeeee ee 8 eeeeeeeeeee ee e eeeeeeeeeee eeeeee. Meee eeeee ee eee eeeee eeeeeeeee ee MeM8(eeeee)M. Mee eeeeeeeee eeeee ee eeeeeeeeeeee eee eeeeee eee eeeeeeee, eeeee eeeee ee eee eeeeee eeeee eee eeeeeeeee eeeeeee. Me eee eeeeeeeee ee MeM8(eeeee)M ee eeeeeeee ee ee eeeeee, ee eee ee eeeeee ee eeeeeee eeee eeeeeee eeeeee eee eeeeeeee. Meeeeeeee, ee ee eeee eeeeee ee eeeeee eeee eeeeeee ee eeeeeeeeeeeeeee.

Me eeeeeee-eeeeeeeee eeeeeeeeeeeeee eeeeeeeeeee eeeeee eee eeeeeeeee eeee, ee eee eeeeeeeee eeeeeeee eeeeeeeee eeee eeeeee eeeeeeeeeeeee eeeee eeee eee eeeeeeeee eeeee ee eeeeeee; eee eeeeeee, eeeeeeeeeeeeeeeee (MM8) ee eee eeee eeeeeeee eeee eeeeeeeeee.[‌88‌,‌88‌] Mee eeeeeeeee ee eeeeeeeee eeee eeeeeeeee ee eeeeeee eeeeeeeee eee eeee. Me eeeee eeeee ee eeeeeee ee eee eeee ee eeeeeeeee ee ee eeeee eeeee ee eeeeeeeee. Mee eeeeeeeeee eeeee ee eeeeee, eeeeeee, ee eeeeeeeeeeeeeeee. Me eeeeeee-eeeeeeeee eeeeeeeeeeeeee eeeeeeee(8,8-eee-eeeeeeeeeeeeeeeeeeeee)eeeeee (MMMM) ee eeeee eeee

Mee eeeeeeeeee-eeeee eeeeeeeee, eeeeeee ee eeeee eeeeeeeeee eee eee eeeeee ee e eeeeeeee eeee eee eeeeeeee e eeeeee ee eeeeeeeeee ee eee eeeeeeeee eeeeeeeee eeeeeee eeeeeee e eeeeeeee eeeeee. Meeeeee, eee eeeeeeeee eeee eeee ee eeeeeee eeeeeeeeee eeeeeeeeee ee eeeeeeee, eeee eeeeeeeee eee eeee ee ee eeeeeeeee ee eeee ee eeeeeeeeee eeeeeeee eeeeee. Meee ee eee ee eeeee eeeee ee eeeeeee eeeeeeeeeeeee eeeeeeee eeee eeeeee e eeeee eeeeeeeee eeeee.[‌8‌,‌88‌]

Meeeeeeeeee eeeeeee, eeee ee eeeeeeeeee eee eeeeeeeeeeeeeeee, eee ee eeeeeeeeeee eeeeeee, eee eeee eee ee eeeeeeeee.[‌88‌‌88‌] Me eeeeeeee, ee ee eeeeeeee ee eee eeeeeeeeeee eeeeeee eeee eee eeeeeeeee eeeeeeeeeee eeeeeee eee eeee ee eee eeee eeee.[‌88‌‌88‌]

Meeeeeeeeee ee eeeeeeeee ee eeeeee eeeeeeeee eeeeeee eeeeeeee eee eeeeeeeeee eeeeeeeeeeeee eee ee eeeee ee Meeeeee ee Meeeeeeee, Mee.88e [MeeeeM (M=M, M) (Meeeeeee eee], eee eeeeeeeee ee eeeeeeee eeeeeeee eeeeee eeeee eeeeeeeee eee ee eeeee Meeeeee ee Meeeeeeee, Mee.8 [Meeeeeeee eeee Meeeeeeeee MeeeeMeeeee π-Meeee eee Meeeeeeee ee Meeeee 888 (Me, Me, Me, Me, Me, Me, Me, Me, Me) (Meeeeee]. Meeeeeeeee eeeeeeeeeeeee eeeeeeeee ee M=M eeeee eee eeee eeeeeeeee ee Meeeeee ee Meeeeeeee, Mee.88e [Meeee MeeeeeMeeeeeeeee Meeee: Meee Meeeeee; Meeeeeeeee Meeee eee Meee Meeee (Meeeeee], Mee.88 [Meeee MeeeeeMeeeeeeeee Meeee: Meeeee eee Meeeeeeeeee; Meeeeeee; Meeeeee (Meeeeee], eee Mee.88 [Meeeeeeeeeeeeeee Meeeeeeee (eeee. MMM eee MMM) (Meeeeeee eee].