Skip to main content
. Author manuscript; available in PMC: 2008 Dec 1.
Published in final edited form as: J Org Chem. 2007 Apr 12;72(10):3896–3905. doi: 10.1021/jo070321u

Table 4.

Diastereoseletive Formation of 2,5-Cis-Pyrrolidinesa

graphic file with name nihms62275f6.jpg
entry substrate method, temp, time yield (%)c40 yield (%)c41
1 39a, R1 = i-Pr, R2 = Me oil bath, 190 °C, 72 h 49 25
2 39a 210 °C (μW), 3 h 51 28
3 39a oil bath, 200°C, 3 h 40 19
4 39b, R1 = i-Pr, R2 = OMe oil bath,190 °C, 72 h 49 23
5 39b 210 °C (μW), 3 h 51 23
6 39b oil bath, 190 °C, 72 hb 33 24
7 39c. R1 = t-Bu, R2 = Me oil bath, 170 °C, 72 h 34 15
8 39c 210 °C (μW), 3 h 31 17
9 39d, R1 = Me, R2 = Me oil bath, 200 °C, 72 h 48 15
10 39d 210 °C (μW), 3 h 48 15
11 39e, R1 = i-PrCH2, R2 = Me oil bath, 200 °C, 72 h 49 20
12 39e 210 °C (μW), 3 h 49 19
13 39f, R1 = Bn, R2 = Me oil bath, 200 °C, 72 h 50 22
14 39f 210 °C (μW), 3 h 47 21
a

Sulfonamides 39 were dissolved in DMF (0.1 M) and treated with Cs2CO3 (1 equiv) and Cu(ND)2 (3 equiv) and were heated in the indicated manner at the indicated temperature and time.

b

Reaction run with NaH as base instead of Cs2CO3: Sulfamide 39b in DMF was treated with NaH (1.2 equiv) at 23 °C for 0.5 h, then Cu(ND)2 (1.2 equiv) in DMF was added, stirred 0.5 h, reaction was then heated at 190 °C for 72 h.

c

Yields refer to isolated products, diastereomeric ratios (>20 :1) were determined by analysis of the crude 1H NMR and by isolated yields. ND = neodecanoate.