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. Author manuscript; available in PMC: 2008 Sep 9.
Published in final edited form as: Org Lett. 2006 Jul 6;8(14):3113–3116. doi: 10.1021/ol061216u

Table 2.

2-(Allenyl)phenylazide cyclization results

graphic file with name nihms61170f6.jpg
entry R R1 R2 yield 7(%)a yield11(%)a Ratio7:10b
a H H CH3 40 56 1:1.2
b H H CH2OTBS 22 29 1.2:1
c H H CH2CH2OTBS 52 43 1.5:1
d H H t-Bu 57 20 2.7:1
e Ph H CH3 40 30 1:1.2
f CH3 H CH3 36 36 1:1.3
g H Ph CH3 - - 35 (10g) 1:1.1
h –(CH2)4– CH3 36 51 1:1.4
i –(CH2)3– CH3 - - 40 (10i) 1:1.5
a

Yield for chromatographically pure, characterized material.

b

Ratio by 1H NMR analysis of the crude thermoslyate.