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. Author manuscript; available in PMC: 2014 Aug 16.
Published in final edited form as: Org Lett. 2004 Nov 11;6(23):4231–4233. doi: 10.1021/ol0482893

Table 2.

Generality of the Catalyzed P-3CCR Using Cu(II) Indan Pybox Catalyst

graphic file with name nihms460836u4.jpg
entrya R1 R2 R3 product % yieldb % eec
  1 PhCH2 (9) 2-furyl (10) PhCH2 (11) 16 83 62 (R)d
  2 PhCH2 (9) BnOCH2 (6) PhCH2 (11) 17 87 72
  3 Ph (5) 2-thiophenecarboxyl (12) t-butyl (13) 18 95 82 (R)
  4 Ph (5) BnOCH2 (6) n-butyl (14) 19 87 88
  5 Ph (5) BnOCH2 (6) n-pentyl (15) 20 83 89
  6 Ph (5) BnOCH2 (6) PhCH2 (11) 21 89 93
  7 Ph (5) BnOCH2 (6) t-butyl (13) 22 95 98
  8 Ph (5) 2-furyl (10) p-MeOPh (7) 23 98 91 (R)
  9 Ph (5) 2-furyl (10) PhCH2 (11) 24 90 75 (R)
10 Ph (5) 2-furyl (10) t-butyl (13) 25 97 89 (R)
11 Ph (5) 2-furyl (10) n-butyl (14) 26 82 78 (R)
12 Ph (5) 2-furyl (10) n-pentyl (15) 27 82 78 (R)
13 Ph (5) 2-thiophenecarboxyl (12) p-MeOPh (7) 28 95 89 (R)
14 Ph (5) 2-thiophenecarboxyl (12) PhCH2 (11) 29 87 75 (R)
15 Ph (5) 2-thiophenecarboxyl (12) n-butyl (14) 30 76 64 (R)
16 Ph (5) 2-thiophenecarboxyl (12) n-pentyl (15) 31 75 60 (R)
a

[0.15 M] final.

b

Isolated yield.

c

See the Supporting Information for HPLC conditions.

d

Inferred absolute stereochemistry based on X-ray crystal analysis with 5-bromo-2-furaldehyde as the substrate.