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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106
Methods of Non-α-Amino Acid Synthesis, Second Edition
A chiral, nonracemic heterocyclic intermediate (oxazolidine 107) was prepared
from 2R-phenyl-2-aminoethanol (106). A Reformatsky type reaction
69
(also see
Chapter 4, Section 4.4) proceeded with ring opening and led to 108. Catalytic hydro-
genation cleaved the benzylic auxiliary to give 109 (ethyl 3-aminopentanoate) in
55% overall yield (72%ee, R).
70
Both ethyl 3-aminobutanoate and ethyl 3-aminohep-
tanoate were prepared by this method.
NHBn
OH
O
N
N
OH
Et
CO
2
Et
Ph
Ph
Et
Ph
Bn
Bn
CO
2
Et
Et
H
2
N
EtCHO, MS
1. BrCH
2
CO
2
Et
Zn, ether
2. aq. NH
4
Cl
H
2
,10% Pd-C
EtOH, RT
9 bar, 24 h
106
107
108
109
CH
2
Cl
2
Conjugate addition of the ...
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