October 2013
Intermediate to advanced
242 pages
9h 22m
English
Content preview from Methods of Non-a-Amino Acid Synthesis, 2nd Edition
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101Diastereoselective and Enantioselective Syntheses
3-amino-4-cyclohexyl-2R-hydroxybutanoic acid, 68, as a mixture of diastereomers
(7:3 2R,3S:2S,3S) in 60% overall yield.
51
Bu
2
N
OH
CHOBu
2
N
H
2
N
CO
2
H
OH
1. H
2
, Rh/Al
2
O
3
18 h
1. HCN, 0°C
2. 23% HCl
reux, 11 h
66 67
68
2. SO
3
•Py, DMSO
25°C
The use of L-serine as a template incorporates a hydroxyl group that may be
manipulated to incorporate other functional groups and used to generate new amino
acids. The amino group of serine was converted to a bromine, for example, with
complete retention of conguration by reaction with NOBr to give S-69.
52
Upon
treatment with ammonium hydroxide, epoxide 70 was generated ...
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