Page 9 - Catalysts for Fine Chemical Synthesis Vol 1 - Robert & Poignant
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viii contents
9.4.2 Synthesis of 1,2-bis(tert-butylmethylphosphino)
ethaneruthenium bromide (BisP*ÿRu) . . . . . 125
9.4.3 Synthesis of (R)-(±)-methyl
3-hydroxypentanoate using (BisP*ÿRu) . . . . . 126
9.5 (1S,3R,4R)-2-Azanorbornylmethanol, an efficient
ligand for ruthenium-catalysed asymmetric
transfer hydrogenation of aromatic ketones
Diego A. Alonso and Pher G. Andersson . . . . . . . . 127
9.5.1 Synthesis of ethyl(1S,3R,4R)-2-
[(S)-1-phenylethylamino]-2-azabicyclo[2.2.1]
hept-5-ene-3-carboxylate . . . . . . . . . . 129
9.5.2 Synthesis of (1S,3R,4R)-3-hydroxymethyl-
2-azabicyclo[2.2.1]heptane . . . . . . . . . . 131
9.5.3 Ruthenium-catalysed asymmetric transfer
hydrogenation of acetophenone . . . . . . . . 133
References . . . . . . . . . . . . . . . . . . . . . 134
10 Asymmetric Reduction of Ketones Using Bakers' Yeast . . . . 137
10.1 Bakers' yeast reduction of ethyl acetoacetate . . . . . 137
10.2 Enantioselective synthesis of cis-N-carbobenzyloxy-3-
hydroxyproline ethyl ester
Mukund P. Sibi and James W. Christensen . . . . . . 140
10.2.1 Immobilization of bakers' yeast . . . . . . . 140
10.2.2 Bakers' yeast reduction of cis-N-
carbobenzyloxy-3-ketoproline ethyl ester . . . . 140
References . . . . . . . . . . . . . . . . . . . . . 142
11 Asymmetric Reduction of Ketones Using
Nonmetallic Catalysts. . . . . . . . . . . . . . . . 143
11.1 Introduction . . . . . . . . . . . . . . . . . . 143
11.2 Oxazaborolidine borane reduction of acetophenone . . . 146
11.3 Oxazaphosphinamide borane reduction of
chloroacetophenone . . . . . . . . . . . . . . . 148
11.4 Asymmetric reduction of chloroacetophenone using
a sulfoximine catalyst . . . . . . . . . . . . . . 151
11.4.1 Preparation of b-hydroxysulfoximine
borane . . . . . . . . . . . . . . . . 151
11.4.2 Reduction of chloroacetophenone using
the sulfoximine borane . . . . . . . . . . 153
11.4.3 Summary . . . . . . . . . . . . . . . 155
11.5 Asymmetric reduction of bromoketone catalysed
by cis-aminoindanol oxazaborolidine
Chris H. Senanayake, H. Scott Wilkinson and
Gerald J. Tanoury. . . . . . . . . . . . . . . 157
