SUPPORTING INFORMATION. Organocatalytic asymmetric intramolecular aza-henry reaction: Facile synthesis of trans-2,3-disubstituted tetrahydroquinolines
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1 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 SUPPORTIG IFORMATIO Organocatalytic asymmetric intramolecular aza-enry reaction: Facile synthesis of trans-2,3-disubstituted tetrahydroquinolines Rajendra Maity and Subhas Chandra Pan * Department of Chemistry, Indian Institute of Technology Guwahati, orth Guwahati, Assam, span@iitg.ernet.in Table of Contents 1. General procedure of the synthesis of nitro-amine S2 2. Catalyst, solvent and temperature screening S3-S6 3. Crystal data S7-S8 4. Absolute configuration and References S9 5. MR data S10-S28 6. PLC data S29-S53 S1
2 General procedure for the synthesis of nitro-amine: R CO O 2 S 1 R= -, -5Cl, -6Cl, 1.MeO 2, 1M ao; 8M Cl 2.MsCl, DIPEA O 2-4Me 2, -5CF 3 S 2 80% R O 2 O C 2 O 100 o C, neat O OC 2 5 R O 2 2, Pd/C,MeO R O 2 O 2 2 S 3 80% S 4 75% S 2, S 4 were prepared by previously reported procedure 1, S 3 was prepared by previously reported procedure 2. S2
3 Preliminary Catalyst screening: 2 O 2 + PhCO Catalyst (10mol%) C 2 Cl 2 :pentane (1:5) 0.2 M, 3days,RT O 2 CF 3 CF 3 S S O O CF 3 75% Yield -60 ee CF 3 55% Yield 00 ee CF 3 o reaction CF 3 O O O o reaction CF 3 CF 3 Bui ibu O S 55% Yield 5% ee Bn O S o reaction O O O O S CF 3 CF 3 MeO P O O O 30% Yield o ee 70% Yield o ee o reaction MeO MeO MeO CF 3 CF 3 O O S O S TBDPSO 47% Yield 37%ee CF 3 45% Yield 30%ee CF 3 50% Yield 5%ee MeO MeO MeO O S O S 70% Yield 69% ee F 3 C CF 3 50% Yield 6% ee MeO OMe 60% Yield 5% ee S3
4 MeO O MeO S ibu S S 60% Yield 7% ee O ibu F 3C CF 3 80% Yield 67% ee F 3C CF 3 73% Yield 42% ee MeO S S S 85% Yield -60% ee F 3 C CF 3 F 3 C CF 3 80% Yield -60% ee F 3C CF 3 81% Yield 55% ee MeO S F 3C 85% Yield 74% ee CF 3 S4
5 Preliminary solvent screening using catalyst (V): O PhCO Catalyst V (10 mol%) Solvent (0.2 M), RT, 3days O 2 Ph o. Solvent Yield (%) a ee b 1. Ethanol Toluene CCl C 2 Cl Benzene PhCF Chlorobenzene Ether MTBE CCl Dichloroethane Cyclohexane:C 2 Cl 2 (5:1) n-exane:c 2 Cl 2 (5:1) Pentane:C 2 Cl 2 (5:1) eptane:c 2 Cl 2 (5:1) exane:ccl 3 (5:1) Benzene (MS 4 A o ) Benzene:CCl 3 (5:1) a Isolated yield after silica gel column chromatography. b Determined by PLC using stationary phase chiral column. S5
6 Preliminary temperature screening using the catalyst V: O 2 ΝΗ 2 + PhCO Catalyst V(10 mol%) Pentane:C 2 Cl 2 (5:1) Temp., 3 days Trans (a) O 2 + Cis (b) O 2 o Temp. Overall Yield dr(a:b) ee (a) 1 RT 85% 100:0 74% 2 0 o C 85% 1:1 80% 3-20 o C 85% 1:1 80% S6
7 CRYSTAL DATA OF COMPOUD (CCDC ) 3f: ORTEP STRUCTURE Crystal data and structure refinement for CIRAL COMPOUD 3f Identification code RM-O2-4Br-CIRAL Empirical formula C Br 2 O 2 Formula weight Temperature/K 296(2) Crystal system orthorhombic Space group P a/å 5.947(3) b/å 7.118(3) c/å (11) α/ β/ γ/ Volume/Å (10) S7
8 Z 4 ρ calc mg/mm m/mm F(000) Crystal size/mm Θ range for data collection 2.48 to Index ranges -7 h 7, -8 k 7, -36 l 40 Reflections collected Independent reflections 2607[R(int) = ] Data/restraints/parameters 2607/0/181 Goodness-of-fit on F Final R indexes [I>=2σ (I)] R 1 = , wr 2 = Final R indexes [all data] R 1 = , wr 2 = Largest diff. peak/hole / e Å /-0.51 Flack parameter (19) S8
9 (2R, 3S)-1,2,3,4-tetrahydro-3-nitro-2-phenylquinoline (3a): O 2 Absolute configuration: The optical rotation of 3a was [α] D 23 = (c 0.17, CCl 3 ). As, it was opposite to the reported compound 3, the absolute configuration was determined to be (2R, 3S). References: 1. J. C. Anderson, A. oble, P. R. Torres, Tetrahedron Lett., 2012, 53, P. Chauhan, K. Kaur,. Bala, V. Kumar, S. S. Chimni, Indian J. Chem., Sect B, 2011, 50B, X.-F. Cai, M.-W. Chen, Z.-S. Ye, R.-. Guo, L. Shi, Y.-Q. Li, Y.-G. Zhou, Chem. Asian J., 2013, 8, S9
10 MR Data of the Products: O 2 3a O 2 3a S10
11 O 2 3b Me O 2 3b Me S11
12 O 2 3c O 2 3c S12
13 O 2 3d O 2 3d S13
14 O 2 3e Cl O 2 3e Cl S14
15 O 2 3f Br O 2 3f Br S15
16 O 2 3g F O 2 3g F S16
17 O 2 3h OMe O 2 3h OMe S17
18 O 2 3i O 2 3i S18
19 O 2 3j Cl O 2 3j Cl S19
20 O 2 3k Br O 2 3k Br S20
21 O 2 3l Me Me O 2 3l Me Me S21
22 O 2 3m O 2 3m S22
23 O 2 3n O 2 3n S23
24 O 2 3o O 2 3o S24
25 Cl O 2 3p Cl O 2 3p S25
26 Cl O 2 3q Cl O 2 3q S26
27 O 2 3r O 2 3r S27
28 F 3 C O 2 3s F 3 C O 2 3s S28
29 PLC data of the Products: O 2 3a O 2 3a S29
30 O 2 3a O 2 3b Me S30
31 O 2 3b Me O 2 3b Me S31
32 O O 2 2 3c O 2 3c S32
33 O 2 3d O 2 3d S33
34 O 2 3e Cl O 2 3e Cl S34
35 O 2 3e Cl O 2 3f Br S35
36 O 2 3f Br O 2 3f Br S36
37 O 2 3g F O 2 3g F S37
38 O 2 3g F O 2 3h OMe S38
39 O 2 3h OMe O 2 3i S39
40 O 2 3i O 2 3i S40
41 O 2 3j Cl O 2 3j Cl S41
42 O 2 3j Cl O 2 3k Br S42
43 O 2 3k Br O 2 3l Me Me S43
44 O 2 3l Me Me O 2 3l Me Me S44
45 O 2 3m O 2 3m S45
46 O 2 3n O 2 3n S46
47 O 2 3o O 2 3o S47
48 Cl O 2 3p Cl O 2 3p S48
49 Cl O 2 3p Cl O 2 3q S49
50 Cl O 2 3q Cl O 2 3q S50
51 O 2 3r O 2 3r S51
52 O 2 3r F 3 C O 2 3s S52
53 F 3 C O 2 3s F 3 C O 2 3s S53
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