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. Author manuscript; available in PMC: 2013 Jul 29.
Published in final edited form as: Org Lett. 2012 Jan 6;14(2):464–467. doi: 10.1021/ol202947f

Table 2.

Thiol scope of cross-coupling reactions on solid phase.

graphic file with name nihms348815u3.jpg

entry thiol (R-SH) product 4-SR-Phe product total cross-coupled productsa
1 graphic file with name nihms348815t1.jpg 2 22% 99%
2 graphic file with name nihms348815t2.jpg 5 90% 90%
3 graphic file with name nihms348815t3.jpg 6 2% 2%
4 HS-(CH2)7-CH3 0% 0%
5 graphic file with name nihms348815t4.jpg 7 21 %b 45%b
6 graphic file with name nihms348815t5.jpg 2 57%b 67%b
a

Includes disulfide products;

b

at 100 °C. RN = Ac-Thr(tBu)- (solid) or Ac-Thr- (solution). RC = -Pro-Asn(Trt)-NHRink (solid) or -Pro-Asn-NH2 (solution).