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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46
Methods of Non-α-Amino Acid Synthesis, Second Edition
catalyzed by a chiral rhodium complex,
27
gave the N-protected lactam 35 [BTMSM
= bis(trimethylsilylmethyl); L = MEOX
28
]. Deprotection generated lactam 36, which
was hydrolyzed to give 4-amino-3-phenylbutanoic acid with good enantioselectivi-
ty.
29
See Chapter 5 for other asymmetric amino acid syntheses.
N
N
2
H
Ph
O
BTMSM
N
O
BTMSM
Ph
N
O
H
Ph
2% Rh
2
L
4
, DCM
reux
KF, H
2
O, aq. DMSO
34
35
36
Hydroxy-substituted amino acids are prepared from an appropriately substituted
lactam. Sodium borohydride reduction of the ketone moiety in lactam 37 gave 38.
Subsequent basic hydrolysis of the lactam gave 4-hydroxy-5-aminopent ...
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