. Author manuscript; available in PMC: 2014 Oct 8.

Published in final edited form as: J Org Chem. 2008 Jan 30;73(5):1774–1782. doi: 10.1021/jo702334z

Table 3.

Regioselectivity in the thiocarbonylation of 4,6-benzylidene β-methyl glucoside.^a,b

Entry	Catalyst	32 (%)	33 (%)	34 (%)	33 : 34	35 (%)	36 (%)
1	NMI (20 mol%)	-	7	13	1 : 2	76	4
2	NMI (20 mol%) + FeCl₃(15 mol%)	5	11	18	1 : 1.6	38	28

3	27 (20 mol%)	-	18	27	1 : 1.5	25	30
4	27 (20 mol%) + FeCl₃(15 mol%)	9	33	23	1.4 : 1	7	29

5	28 (20 mol%)	7	14	10	1.5 : 1	36	33
6	28 (20 mol%) + FeCl₃(15 mol%)	15	10	18	1 : 2	4	54

All reactions conducted in the presence of PEMP, and run according to the standard conditions described in the Experimental Section.

Conversion determined by ¹H NMR.

27: BOC-Pmh-DPro-Aib-DTrp(Boc)-DPhe-OMe

28: BOC-Pmh-Thr(tBu)-DVal-His(trt)-DPhe-DVal-Thr(tBu)-Ile-OMe