Table 1. Results of diastereoselective duplex formations between chiral amidine dimers (3a-4c) and racemic carboxylic acid dimers (rac-1a and rac-2a).
| Amidine dimer (amide sequence) |
rac-2a (CONH-cHex) |
rac-1a (NHCO-cHex) |
||||
|---|---|---|---|---|---|---|
| Run | d.e. (%)* | Suppl.† Fig. no. | Run | d.e. (%)* | Suppl.† Fig. no. | |
| (R,R,R,R,R,R)-3a (CONH-cHex) | 1 | 58 (R,R) | 25 | 6 | 14 (S,S) | 40 |
| (R,R,S,S,R,R)-3b (CONH-cHex) | 2 | >99 (S,S) | 27 | 7 | 64 (R,R) | 42 |
| (R,R)-3c (CONH-cHex) | 3 | >99 (R,R) | 34 | 8 | 64 (S,S) | 44 |
| (R,R)-3d (CONH-cHex) | 4 | >99 (R,R) | 36 | 9 | 68 (S,S) | 46 |
| (R,R,meso,R,R)-3e (CONH-cHex) | 5 | 0 | 38 | 10 | 0 | 48 |
| (R,R,R,R,R,R)-4a (NHCO-cHex) | 11 | 70 (S,S) | 50 | 14 | 64 (R,R) | 56 |
| (R,R,S,S,R,R)-4b (NHCO-cHex) | 12 | 34 (R,R) | 52 | 15 | 74 (S,S) | 58 |
| (R,R)-4c (NHCO-cHex) | 13 | 80 (S,S) | 54 | 16 | 70 (R,R) | 60 |
*Estimated using 1H NMR (CDCl3, 25 °C).
†Supplementary Fig. no.