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. Author manuscript; available in PMC: 2009 Jan 30.
Published in final edited form as: Synlett. 2006 Nov 13;2007(4):571–582. doi: 10.1002/ejoc.200600767

Table 4.

N-Aryl pyrrolidine synthesis

graphic file with name nihms-87961-t0046.jpg
Entry R R1 R2 R3 R4 Ligand Ratio 35:36 dr Yielda
1 graphic file with name nihms-87961-t0047.jpg OMe H H H Dppb 35:1 - 75%
2 graphic file with name nihms-87961-t0048.jpg CN H H H Dppb >100:1 - 86%
3 graphic file with name nihms-87961-t0049.jpg OMe Me H H Dppe 10:1 >20:1 66%
4 graphic file with name nihms-87961-t0050.jpg OMe H Ph H Dppe 8:1 2:1 88%
5 graphic file with name nihms-87961-t0051.jpg OMe H H Ph Dppe 10:1 >20:1 68%
6 graphic file with name nihms-87961-t0052.jpg H H H H P(2-furyl)3 >20:1 - 88%
7 graphic file with name nihms-87961-t0053.jpg OMe Me H H P(2-furyl)3 7:1 >20:1 79%
8 graphic file with name nihms-87961-t0054.jpg OMe H H Ph P(2-furyl)3 >20:1 10:1 55%
a

Conditions: 1.0 equiv amine, 1.1-2.0 equiv R-Br, 1.2 equiv NaOtBu, 1 mol % Pd2(dba)3, 2-4 mol % ligand, toluene (0.25 M), 60-110 °C.