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. Author manuscript; available in PMC: 2013 Nov 16.
Published in final edited form as: Org Lett. 2012 Oct 25;14(22):5632–5635. doi: 10.1021/ol302409g

Table 2.

THF cyclization via Pd-AAA approach

graphic file with name nihms417830t2.jpg
entry conditions yielda
(conversion)		 drb
(23:24)
1 L1 (S,S), rt, 0.15 M traces -
2 L1 (S,S), 50 °C, 0.15 M 75% (100%) 1:4
3 L1 (R,R), 50 °C, 0.15 M 77% (100%) 4:1
4 L1 (R,R), 35 °C, 0.15 M (58%) 3.3:1
5 L1 (R,R), 50 °C, Et3B, 0.15 M (100%) 1.2:1
6 L1 (R,R), 50 °C, Et2Zn, 0.15 M (90%) 1:2
7c L1 (R,R), 50 °C, Et3N, 0.15 M 82% (100%) 4.6:1
8 L1 (R,R), 66 °C, Et3N, 0.15 M (100%) 3.5:1
9 L1 (R,R), 50 °C, EtN(i-Pr)2, 0.15 M (< 10%) -
10d L1 (R,R), 50 °C, AcOH, 0.15 M (100%) 3.6:1
11 L1 (R,R), 50 °C, Et3N, 0.4 M (100%) 3.7:1
12 L1 (R,R), 50 °C, Et3N, 0.05 M (100%) 4:1
a

Isolated yield.

b

dr determined from the 1H NMR of the crude mixture.

c

< 5% formation of the undesired byproduct.

d

30% formation of the undesired byproduct.