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. Author manuscript; available in PMC: 2013 Dec 21.
Published in final edited form as: Org Lett. 2012 Nov 30;14(24):6290–6293. doi: 10.1021/ol3030555

Table 2.

Iodolactonization of 6-Substituted-5(Z)-hexenoic Acidsa

graphic file with name nihms426051u3.jpg
entry R product yieldb (%) erc,d
ae Ph 8a 89 99:1
bf,g p-NC-C6H4 8b 88 99:1
cg 2-Np 8c 93 98.5:1.5
d t-Bu 8d 98 98:2
a

Reactions run on 0.1 mmol scale.

b

Isolated yield after column chromatography.

c

er determined by chiral HPLC.

d

Absolute stereochemistry of 8a–d are based on analogy with 6c and 6e.

e

Z/E ratio of 7a, 14:1.

f

Z/E ratio of 7b, 20:1.

g

Results obtained after 38 h at −20 °C.