Page 10 - Catalysts for Fine Chemical Synthesis Vol 1 - Robert & Poignant
P. 10
contents ix
11.5.1 Synthesis of aminoindanol oxazaborolidine . . . 157
11.5.2 Asymmetric reduction of 2-bromo-
(3-nitro-4-benzyloxy)acetophenone . . . . . . 157
11.5.3 Conclusions . . . . . . . . . . . . . . 159
11.5.4 Stereoselective reduction of
2,3-butadione monoxime trityl ether . . . . . 161
11.5.5 Stereoselective reduction of methyl
3-oxo-2-trityloxyiminostearate . . . . . . . 163
11.5.6 Stereoselective reduction of 1
-(tert-butyldimethylsilyloxy)-3-oxo-2-
trityloxyiminooctadecane . . . . . . . . . 164
11.6 Enantioselective reduction of ketones using
N-arylsulfonyl oxazaborolidines
Mukund P. Sibi, Pingrong Liu and Gregory R. Cook. . . 166
11.6.1 Synthesis of N-(2-pyridinesulfonyl)-1-amino-
2-indanol . . . . . . . . . . . . . . . 166
11.6.2 Asymmetric reduction of a prochiral ketone
(chloroacetophenone) . . . . . . . . . . 167
11.7 Reduction of ketones using amino acid anions
as catalyst and hydrosilane as oxidant
Michael A. Brook . . . . . . . . . . . . . . . . 169
References . . . . . . . . . . . . . . . . . . . . . 172
12 Asymmetric Hydrogenation of Carbon±Carbon Double
Bonds Using Organometallic Catalysts . . . . . . . . . . 175
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
12.4.1 ÿ . . . . . . 180
Preparation of (COD) Rh BF 4
2
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
