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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 8.

Synthesis of azabicyclo[3.3.0]octanes

graphic file with name nihms-87961-t0088.jpg
Entry R Ar R1 R2 Yielda
1b CN p-C6H4Me H Ar 69%
2b CO2t-Bu p-C6H4OMe H Ar 58%
3c H p-C6H4CN Ar H 76%
4c Cl p-C6H4CO2t-Bu Ar H 71%
a

Conditions: 1 equiv amine, 1.4 equiv ArBr, 1.2 equiv NaOtBu, 1 mol % Pd2(dba)3, 2 mol % ligand, toluene (0.25 M), 110 °C. All products were obtained with >20:1 dr.

b

Ligand = 2-diphenylphosphino-2′-(N,N-dimethylamino)biphenyl.

c

Ligand = P(t-Bu)2Me·HBF4.