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M. Rueping, E. Sugiono
Table 8 Scope of the asymmetric BINOL-phosphate catalyzed Strecker reaction
Entry
21 R
R
Yield [%] a
ee [%] b
1
a Bn
4-CF 3 C 6 H 4
75
97
2
b P M B
4 - C F 3 C 6 H 4
53
96
3
c Bn
3,5-(F)-C 6 H 3
59
98
4
d Bn
1-naphthyl
85
99
5
e PMB
4-MeO-1-naphthyl
70
94
6
f Bn
2-naphthyl
71
85
7
g Bn
2-thienyl
77
95
8
h Bn
2-furyl
84
89
9
i Bn
5-CH 3 -2-furyl
85
92
10
j PMB
Phenyl
87
89
11
k Bn
4-CH 3 -C 6 H 4
97
93
12
l Bn
4-MeO-C 6 H 4
55
87
13
m Bn
4-ClC 6 H 4
69
85
14
n PMB
4-ClC 6 H 4
60
86
15
o Bn
88
93
a Isolated yields of the corresponding acetamide after chromatography
b Enantioselectivities were determined by HPLC analysis
to demonstrate the preparation of these compounds we used established
procedures to afford the p-methoxyphenyl glycine (Sigman et al. 2000)
and the corresponding diamine (Scheme 4; Hassan et al. 1998).
The organocatalytic hydrocyanation of imines provides direct access
to a diverse range of aromatic amino nitriles and the corresponding
amino acids and diamines in highest enantioselectivities. The use of