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. Author manuscript; available in PMC: 2019 Mar 11.
Published in final edited form as: Org Lett. 2015 Feb 25;17(5):1082–1085. doi: 10.1021/ol503425t

Table 1.

Substrate Scope of α-Quaternary Cyclic Hydroxamic Acid Derivativesa

graphic file with name nihms-1015128-t0003.jpg
entry substrate R yield (%)b ee (%)c
1 graphic file with name nihms-1015128-t0004.jpg Bz (3a→4a)d 98 73
2 Boc (3b4b) 95 72
3 PhO(CO) (3c4c) 95 73
4 graphic file with name nihms-1015128-t0005.jpg Bz (3d→4d) 29 88
5 Piv (3e→4e) 48 73
6 Bn (3f→4f) trace ND
7 Boc (3g4g) 67 85
8 Cbz (3h4h) 89 84
9 PhO(CO) (3i→4i) 70 87
10 graphic file with name nihms-1015128-t0006.jpg 81 93
a

Reaction performed under the conditions of Figure 3 at 60 °C.

b

All reported yields are for isolated products.

c

Enantiomeric excesses were determined by chiral SFC analysis.

d

Absolute configuration was assigned by VCD spectroscopy22 supported by theoretical calculations (see supporting information).