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. Author manuscript; available in PMC: 2012 Jun 26.
Published in final edited form as: Bioorg Med Chem Lett. 2008 Jan 11;18(4):1392–1396. doi: 10.1016/j.bmcl.2008.01.019

Table 1.

Ratios of cis to trans pyrrolines for different combinations of substituents R1, R2 and R3 in the starting materials.

graphic file with name nihms41612u1.jpg
pyrroline mixture R1 R2 R3 cis : trans ratio
ct-1 Ph p-O2N-C6H5 Ph 1 : 2
ct -2 Ph p-O2N-C6H5 p-MeO-C6H5 1 : 2
ct -3 Ph p-O2N-C6H5 p-O2N-C6H5 1 : 1.4
ct -4 Ph p-F-C6H5 Ph 1 : 1.6
ct -5 Ph p-F-C6H5 p-MeO-C6H5 1 : 1.8
ct -6 Ph p-F-C6H5 p-O2N-C6H5 1 : 1.7
ct -7 Ph p-Me-C6H5 Ph 1 : 1.9
ct -8 Ph p-Me-C6H5 p-MeO-C6H5 1 : 1.7
ct -9 Ph p-Me-C6H5 p-O2N-C6H5 1 : 1.7
ct -10 Ph 2,4,6-i Pr-C6H5 Ph 1 : 1.7
ct -11 Ph 2,4,6-i Pr-C6H5 p-MeO-C6H5 1 : 2
ct -12 Ph 2,4,6-i Pr-C6H5 p-O2N-C6H5 1 : 1.9
ct -13 Ph p-MeO-C6H5 Ph 1 : 1.9
ct -14 Ph p-MeO-C6H5 p-MeO-C6H5 1 : 1.6
ct -15 Ph p-MeO-C6H5 p-O2N-C6H5 1 : 1.7
ct -16 Ph graphic file with name nihms41612t1.jpg Ph 1 : 1.2
ct -17 Ph graphic file with name nihms41612t2.jpg p-MeO-C6H5 1 : 1.7
ct -18 Ph graphic file with name nihms41612t3.jpg p-O2N-C6H5 1 : 1.4
ct -19 Ph Bu Ph 1 : 1.7
ct -20 Ph Bu p-MeO-C6H5 1 : 2
ct -21 Ph Bu p-O2N-C6H5 1 : 1.4
ct -22 Ph Me Ph 1 : 1.4
ct -23 Ph Me p-MeO-C6H5 1 : 1.5
ct -24 Ph Me p-O2N-C6H5 1 : 1.3
ct -25 p-Br-C6H5 p-Me-C6H5 Ph 1 : 1.6
ct -26 p-Br-C6H5 p-MeO-C6H5 Ph 1 : 1.5
ct -27 p-Br-C6H5 p-O2N-C6H5 Ph 1 : 1.5
ct -28 p-MeO-C6H5 p-Me-C6H5 Ph 1 : 1.6
ct -29 p-MeO-C6H5 p-MeO-C6H5 Ph 1 : 1.4
ct -30 p-MeO-C6H5 p-O2N-C6H5 Ph 1 : 1.6