Page 187 - Catalysts for Fine Chemical Synthesis Vol 1 - Robert & Poignant

Catalysts for Fine Chemical Synthesis: Hydrolysis, Oxidation and Reduction. Volume 1
Edited by Stan M Roberts and Geraldine Poignant
Copyright  2002 John Wiley & Sons, Ltd.
ISBN: 0-471-98123-0

12 Asymmetric Hydrogenation of
Carbon±Carbon Double Bonds

Using Organometallic Catalysts

CONTENTS
12.1 Introduction . . . . . . . . . . . . . . . . . . . . 176
12.2 Hydrogenation of dimethyl itaconate using [Rh((S,S)-Me-BPE)]. . . . . 177
12.3 Hydrogenation of an a-amidoacrylate using
[Rh((R,R)-Me-DuPHOS)] . . . . . . . . . . . . . . . . . 179
12.4 Hydrogenation of an a-amidoacrylate using [Rh(B[3.2.0]DPO)]
complexes . . . . . . . . . . . . . . . . . . . . . 180
ÿ
‡ . . . . . . . . . . . . . 180
12.4.1 Preparation of (COD) 2 Rh BF 4
12.4.2 Preparation of the bisphosphinite ligand . . . . . . . . . . . 182
12.4.3 Asymmetric reduction of a-acetamido cinnamic acid . . . . . . . 184
12.5 Hydrogenation of enol carbonates and 4-methylene-n-acyloxazolidinone
using [Rh((R)-BiNAP)] complexes . . . . . . . . . . . . . . 186
P.H. Dixneuf, C. Bruneau and P. Le gendre
12.5.1 Synthesis of (S)-4,4,5-trimethyl-1,3-dioxolane-2-one . . . . . . . . 186
12.5.2 Synthesis of (S)-2-methyl-2,3-butanediol . . . . . . . . . . . 187
12.5.3 Preparation of optically active N-acyloxazolidinones . . . . . . . 188
12.5.4 Synthesis of (R)-N-propionyl-4,5,5-trimethyl-1,3-oxazolidin-2-one . . . 189
12.6 Enantioselective ruthenium-catalyzed hydrogenation of
vinylphosphonic acids . . . . . . . . . . . . . . . . . 190
V. Ratovelomanana-vidal, J.-P. GenE Ã t
12.6.1 Synthesis of chiral Ru(II) catalysts . . . . . . . . . . . . . 190
12.6.2 Asymmetric hydrogenation of vinylphosphonic acids carrying a
phenyl substituent at C 2 . . . . . . . . . . . . . . . . 191
12.6.3 Asymmetric reduction of a vinylphosphonic acid
carrying a naphthyl substituent at C 2 . . . . . . . . . . . . 192
12.6.4 Scope of the hydrogenation reaction . . . . . . . . . . . . 193
12.7 Synthesis of a cylindrically chiral diphosphine and asymmetric
hydrogenation of dehydroamino acids
Jahyo Kang and Jun Hee Lee . . . . . . . . . . . . . . . 194
12.7.1 Preparation of (R,R)-1,1 -bis(a-hydroxypropyl) ferrocene . . . . . . 195
0
12.7.2 Preparation of (R,R)-1,1 -bis[a-(dimethylamino) propyl]ferrocene . . . 196
0
12.7.3 Preparation of (R,R, p S, p S)-1,1 -bis[a-(dimethylamino)propyl]-
0
2,2 -bis(diphenyl-phosphino)ferrocene . . . . . . . . . . . . 197
0
12.7.4 Preparation of (R,R, p S, p S)-1,1 -bis[a-acetoxypropyl)-2,2 0
0
-bis(diphenyl-phosphino)ferrocene . . . . . . . . . . . . . 198
0
0
12.7.5 Preparation of ( p S, p S)-1,1 -bis(diphenylphosphino)-2,2 -bis
(1-ethylpropyl)ferrocene [(S,S)-3-Pt-FerroPHOS] . . . . . . . . 199