Skip to main content
. Author manuscript; available in PMC: 2019 Mar 16.
Published in final edited form as: Org Lett. 2018 Mar 5;20(6):1621–1625. doi: 10.1021/acs.orglett.8b00364

Table 1.

Exploration of VCP substrate scope

graphic file with name nihms965690u2.jpg
entrya R = solventb yield (%)c dr [trans:cis)d er (trans)e er (cis)e
1f,g graphic file with name nihms965690t1.jpg
2-ester
THF 44 78:22 47:53 ND
2 graphic file with name nihms965690t2.jpg
2a
THF 70 40:60 83:17 72:28
3 graphic file with name nihms965690t3.jpg
2b
hex/THF 84 79:21 90:10 75:25
4 THF 82 77:23 88:12 76:24
5f MeOH 82 76:22 70:30 65:35
6 graphic file with name nihms965690t4.jpg
2c
THF 79 68:32 85:15 75:25
7 graphic file with name nihms965690t5.jpg
2d
hex/THF 32 68:32 86:14 75:25
8 graphic file with name nihms965690t6.jpg
2e
hex/THF 77 73:27 90:10 79:21
9 graphic file with name nihms965690t7.jpg
2f
hex/THF 83 80:20 90:10 76:24
10 graphic file with name nihms965690t8.jpg
2g
hex/THF 81 82:18 90:10 73:27
11 graphic file with name nihms965690t9.jpg
2h
hex/THF 94 82:18 90:10 73:27
a

Reactions were performed on a 0.1 mmol scale and were quenched by exposure to air. Reported data is the average of 2 separate experiments, unless noted.

b

Standard conditions: 2:1 hexanes:THF.

c

Isolated yield of a mixture of trans and cis diastereomers.

d

Determined by 1H NMR.

e

Determined by CSP-HPLC (254 nm, uncorrected).

f

Single experiment.

g

dr is crude before purification to remove cis, yield is pure trans.