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. Author manuscript; available in PMC: 2010 Mar 16.
Published in final edited form as: Tetrahedron Asymmetry. 2009 Jan 30;20(1):1–63. doi: 10.1016/j.tetasy.2009.01.002

Table 4.

Formation of α-amino nitriles (1S,6S)-132d–g and (1S,6R)-133d–g from 95d–g.

graphic file with name nihms166053t4.jpg
Entry R Ratio of 129131 Ratio of 132 : 133 :
A: NaCN/TFA		 (1R)-isomers (Yield %)
B: TMSCN/ZnCl2
1 d = Bn 50 : 50 66 : 34 : ND (96) 41 : 59 : ND (89)
2 e = Indma 50 : 50 77 : 23 : ND (56) 33 : 67: ND (48)
3 f = i-Bu 50 : 50 39 : 42 : 19 (86) 18 : 71 : 11 (73)
4 g = t-Bu 20 : 80 16 : 82 : 02 (88) 05 : 90 : 05 (80)
a

Indm = 2-indolylmethyl fragment. ND = (1R)-isomers were not detected by 1H NMR.