=
5.7, 9.5 Hz, 1H), 4.33-4.40 (m, 1H), 7.24 (dd, J = 8.5, 23.0 Hz, 4H), 7.37-7.47 (m, 6H), 7.79 (dd,
J = 7.0, 12.0, 2H), 7.90 (dd, J = 6.9, 11.9 Hz, 2H); HPLC (Chiralpak AS-H column, hexane/iPrOH
-1
8
1 2
0/20, 1.0 mL min , 254 nm): t = 11.4 min (R), t = 26.3 min (S).
3
N-[1-(3-Methoxylphenyl)ethyl]-diphenylphosphinamide (4f): White solid, 96% ee (S),
8
1
[
]
D
= -52.1 (c 1.32, MeOH); H NMR (400 MHz, CDCl
3
): = 1.57 (d, J = 6.8 Hz, 3H), 3.22 (dd, J
=
5.9, 9.5 Hz, 1H), 3.78 (s, 3H), 4.31-4.39 (m, 1H), 6.82-6.88 (m, 3H), 7.21-7.23 (m, 1H),
7
.36-7.47 (m, 6H), 7.80-7.93 (m, 4H); HPLC (Chiralpak AS-H column, hexane/iPrOH 80/20, 1.0
-1
1 2
mL min , 254 nm): t = 14.5 min (R), t = 29.4 min (S).
3
N-[1-(3-Methoxylphenyl)ethyl]-diphenylphosphinamide (4g): White solid, 99% ee (S),
8
1
[
]
D
= -22.1 (c 1.13, MeOH); H NMR (400 MHz, CDCl
3
): = 1.50 (d, J = 6.8 Hz, 3H), 3.69 (s,
3
H), 3.87 (dd, J = 8.0, 10.5 Hz, 1H), 4.36-4.43 (m, 1H), 6.78-6.82 (m, 2H), 6.97 (s, 1H), 7.19 (t, J =
13
7
.7 Hz, 1H), 7.33-7.38 (m, 6H), 7.72 (dd, J = 7.3, 11.9 Hz, 2H), 7.79 (dd, J = 7.1, 11.8 Hz, 2H);
): = 25.1, 49.6, 55.4, 111.2, 121.0, 128.3 (d, J = 7.0 Hz), 128.5, 131.7,
31.8, 128.1 (d, J = 108.6 Hz), 131.7, 131.8, 132.0 (d, J = 9.3 Hz), 132.8 (d, J = 9.4 Hz), 133.0,
C
NMR (100 MHz, CDCl
3
1
1
3
1
33.1, 133.8 (d, J = 119.7 Hz), 157.0; P NMR (162 MHz, CDCl
3
): = 22.9; HRMS Calculated for
21 2
C H22NO
P (M+1) 352.1461, found 352.1451; HPLC (Chiralpak AS-H column, hexane/iPrOH
-1
8
0/20, 1.0 mL min , 254 nm): t
N-(1-Naphthalen-1-yl-ethyl)-diphenylphosphinamide (4h): White solid; H NMR (400
MHz, CDCl ): = 1.70 (d, J = 6.7 Hz, 3H), 3.35-3.38 (m, 1H), 5.23-5.25 (m, 1H), 7.26-7.27 (m,
H), 7.41-7.51 (m, 7H), 7.62 (m, 1H), 7.74-7.78 (m, 3H), 7.86-7.93 (m, 4H).
1 2
= 11.9 min (R), t = 21.3 min (S).
2
1
3
2
2
,3
N-(1-Naphthalen-2-yl-ethyl)-diphenylphosphinamide (4i): White solid, 93% ee (S),
8
1
[
]
D
= -77.8 (c 1.02, MeOH); H NMR (400 MHz, CDCl
3
): = 1.66 (d, J = 6.7 Hz, 3H), 3.27-3.31
(
m, 1H), 4.51-4.61 (m, 1H), 7.32-7.33 (m, 2H), 7.43-7.48 (m, 7H), 7.65 (s, 1H), 7.80-7.83 (m, 5H),
-1
7
2
.93 (m, 2H); HPLC (Chiralpak AS-H column, hexane/iPrOH 80/20, 1.0 mL min , 254 nm): t
1
=
1.6 min (R), t = 27.7 min (S).
2
3
8
N-(1-Furylethyl)-diphenylphosphinamide (4j): White solid, 87% ee (S), [ ]
D
= -42.1 (c
1
0
1
7
.60, CH
2
Cl
2
); H NMR (400 MHz, CDCl
3
): = 1.60 (d, J = 6.8 Hz, 3H), 3.19 (dd, J = 6.6, 10.3 Hz,
H), 4.38-4.44 (m, 1H), 6.13 (d, J = 3.2 Hz, 1H), 6.28 (dd, J = 1.9, 3.2 Hz, 1H), 7.35 (m, 1H),
.42-7.49 (m, 6H), 7.87-7.95 (m, 4H); HPLC (Chiralpak AS-H column, hexane/iPrOH 80/20, 1.0
-1
1 2
mL min , 254 nm): t = 12.1 min (R), t = 17.0 min (S).
3
8
N-(1-Phenyl-propyl)-diphenylphosphinamide (4k): White solid, 87% ee (S), [ ]
D
= -38.5
1
(c 1.26, MeOH); H NMR (400 MHz, CDCl
3
): = 0.79 (t, J = 7.4 Hz, 3H), 1.80-1.89 (m, 1H),
1
.97-2.04 (m, 1H), 3.25 (dd, J = 6.4, 9.4 Hz, 1H), 4.08-4.11 (m, 1H), 7.14-7.16 (m, 2H), 7.23-7.33
(
m, 5H), 7.42-7.44 (m, 4H), 7.73-7.87 (m, 4H); HPLC (Chiralpak AS-H column, hexane/iPrOH
-1
8
0/20, 1.0 mL min , 254 nm): t
1
= 9.6 min (R), t
2
= 17.7 min (S).
5
15
1
1
-Phenyl-N-tosylethanamine (6a): White solid, 96% ee (S), [ ]
D
= -63.7 (c 0.95, EtOH); H
3
NMR (400 MHz, CDCl ): = 1.43 (d, J = 6.8 Hz, 3H), 2.39 (s, 3H), 4.44-4.48 (m, 1H), 4.77 (d, J =
6
.7 Hz, 1H) 7.09-7.11 (m, 2H), 7.17-7.21 (m, 5H), 7.62 (d, J = 8.2 Hz, 2H); HPLC (Chiralcel OD-H
-1
column, iPrOH/hexane 20/80, 1.0 mL min , 254nm): t
1
= 6.4 min (R), t
2
= 7.4 min (S).
5
15
1
-(4-Fluorophenyl)-N-tosylethanamine (6b): White solid, 96% ee (S), [ ]
D
= -58.2 (c 1.02,
1
EtOH); H NMR (400 MHz, CDCl
3
): = 1.39 (d, J = 6.9 Hz, 3H), 2.39 (s, 3H), 4.42-4.49 (m, 1H),
4
.90 (d, J = 6.6 Hz, 1H), 6.87 (t, J = 8.7 Hz, 2H), 7.05-7.09 (m, 2H), 7.19 (d, J = 8.1 Hz, 2H), 7.60
-1
(d, J = 8.2 Hz, 2H); HPLC (Chiralcel OD-H column, iPrOH/hexane 20/80, 1.0 mL min , 254nm):
t
1
= 6.3 min (R), t = 6.9 min (S).
2
S7