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. 2011 May 5;16(5):3802–3825. doi: 10.3390/molecules16053802

Table 2.

Synthesis of Trisubstituted Oxazolidines.

graphic file with name molecules-16-03802-i002.jpg

Entry R1 R2 Oxazolidine Yield (%)
1 i-Pr OMe (2S, 4S)-3a 59
2 i-Pr OEt (2S, 4S)-3b 75
3 i-Pr OBn (2S, 4S)-3c 63
4 i-Pr OPh (2S, 4S)-3d 22
5 i-Pr Me (2S, 4S)-3e 53
6 i-Pr Ph (2S, 4S)-3f 55
7 i-Pr m,p-Cl2C6H3 (2S, 4S)-3g 28
8 i-Pr m,p-(CH3O)2C6H3 (2S, 4S)-3h 58
9 i-Pr p-FC6H4 (2S, 4S)-3i 63
10 i-Pr 1-naphthyl (2S, 4S)-3j 70
11 i-Pr 2-thienyl (2S, 4S)-3k 37
12 Me OMe (2S, 4S)-4a 68
13 Me OEt (2S, 4S)-4b 68
14 Me OBn (2S, 4S)-4c 64
15 Me OPh (2S, 4S)-4d 14
16 Me Me (2S, 4S)-4e 68
17 Me Ph (2S, 4S)-4f 57
18 Me m,p-Cl2C6H3 (2S, 4S)-4g 41
19 Me m,p-(CH3O)2C6H3 (2S, 4S)-4h 90
20 Me p-FC6H4 (2S, 4S)-4i 27
21 Me 1-naphthyl (2S, 4S)-4j 33
22 Me 2-thienyl (2S, 4S)-4k 25
23 Bn OMe (2S, 4S)-5a 66
24 Bn OEt (2S, 4S)-5b 81
25 Bn OBn (2S, 4S)-5c 76
26 Bn OPh (2S, 4S)-5d 5
27 Bn Me (2S, 4S)-5e 45
28 Bn Ph (2S, 4S)-5f 71
29 Bn m,p-Cl2C6H3 (2S, 4S)-5g 30
30 Bn m,p-(CH3O)2C6H3 (2S, 4S)-5h 98
31 Bn p-FC6H4 (2S, 4S)-5i 51
32 Bn 1-naphthyl (2S, 4S)-5j 96
33 Bn 2-thienyl (2S, 4S)-5k 41
34 CH2OH OMe (±)-6a 38
35 CH2OH OEt (±)-6b 50
36 CH2OH OBn (±)-6c 37
37 CH2OH OPh (±)-6d 8
38 CH2OH Me (±)-6e 29
39 CH2OH Ph (±)-6f 23
40 CH2OH m,p-Cl2C6H3 (±)-6g 12
41 CH2OH m,p-(CH3O)2C6H3 (±)-6h 38
42 CH2OH p-FC6H4 (±)-6i 23
43 CH2OH 1-naphthyl (±)-6j 24
44 CH2OH 2-thienyl (±)-6k 58