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. Author manuscript; available in PMC: 2014 Mar 28.
Published in final edited form as: Org Biomol Chem. 2013 Feb 13;11(12):1921–1924. doi: 10.1039/c3ob27495k

Table 2.

(R)-P-catalyzed Asymmetric aza-MBH Reaction

graphic file with name nihms445361t2.jpg
entrya R1 R2 yield (%)b ee (%)c
1 1b, 5-CH3 Bn 2b', 93 95
2 1c, 5-F Bn 2c', 96 93
3 1d, 5-Cl Bn 2d', 91 99
4 1e, 5-Br Bn 2e', 97 >99
5 1f, 6-CH3 Bn 2f', 88 99
6 1g, 6-Cl Bn 2g', 93 96
7 1h, 6-Br Bn 2h', 93 97
8 1i, 7-F Bn 2i', 87 95
9 1j, 7-Cl Bn 2j', 70 99
10 1k, 7-Br Bn 2k', 78 99
11 1l, 7-CF3 Bn 2l', 70 94
12 1m, 5-Cl, 7-CH3 Bn 2m', 86 >99
13 1n, 4-CH3 Bn trace ndd
14 1o, 4,7-Cl2 Bn trace ndd
15 1p, H Me 2p', 85 95
16 1q, H Allyl 2q', 90 97
17 1r, 5-CH3O Bn 2r, 83 90
18e 1s, H Bn 2s, 86 70
19e 1t, 4,7-Cl2 Bn trace ndd
a

1 (0.1 mmol), MVK (0.2 mmol) and catalyst (0.02 mmol) were stirred in 2 mL of chloroform within 48 h at rt.

b

Isolated yield.

c

Determined by chiral HPLC.

d

Not determined.

e

t-Bu group of Boc moiety in 1a was replaced by ethyl group.