Scope of the reactiona,b.
| ||||||
|---|---|---|---|---|---|---|
| Entry | Major product | R1 | R2 | Yield (%)c | trans : cisd | De (trans) (%)e |
| 1 | trans-(Ss,2R,3R)-3a | H (S-1a) | H (2a) | 67 | 72 : 28 | >99 |
| 2 | trans-(Ss,2R,3R)-3b | 5-Cl (S-1b) | H (2a) | 40 | 64 : 36 | 98 |
| 3 | trans-(Ss,2R,3R)-3c | 5-Br (S-1c) | H (2a) | 65 | 71 : 29 | 90 |
| 4 | trans-(Ss,2R,3R)-3d | 3,5-Cl (S-1d) | H (2a) | 47 | 63 : 37 | 98 |
| 5f | trans-(Ss,2R,3R)-3e | H (S-1e) | H (2a) | 41 | 72 : 28 | 98 |
| 6 | trans-(Ss,2R,3R)-3f | 5-Cl (S-1b) | 4-Cl (2b) | 54 | 77 : 23 | 98 |
| 7 | trans-(Ss,2R,3R)-3g | 5-Br (S-1c) | 4-Cl (2b) | 41 | 77 : 23 | 98 |
| 8 | trans-(Ss,2R,3R)-3h | 3,5-Cl (S-1d) | 4-Cl (2b) | 28 | 56 : 44 | 90 |
| 9f | trans-(Ss,2R,3R)-3i | H (S-1e) | 4-Cl (2b) | 57 | 88 : 12 | 98 |
| 10f | trans-(Ss,2R,3R)-3j | H (S-1e) | 4-Me (2c) | 53 | 56 : 44 | 98 |
| 11 | trans-(Ss,2R,3R)-3k | 5-Br (S-1c) | 4-Me (2c) | 53 | 75 : 25 | 98 |
| 12 | trans-(Ss,2R,3R)-3l | 5-Cl (S-1b) | 4-Me (2c) | 69 | 70 : 30 | 98 |
| 13 | trans-(Ss,2R,3R)-3m | 5-Br (S-1c) | 4-NO2 (2d) | — | — | — |
| 14 | trans-(Rs,2S,3S)-3a | H (R-1a) | H (2a) | 65 | 72 : 28 | 90 |
| 15 | trans-(Rs,2S,3S)-3b | 5-Cl (R-1b) | H (2a) | 69 | 75 : 25 | 98 |
| 16 | trans-(Rs,2S,3S)-3c | 5-Br (R-1c) | H (2a) | 60 | 63 : 37 | 98 |
| 17f | trans-(Rs,2S,3S)-3d | 3,5-Cl (R-1d) | H (2a) | 55 | 68 : 32 | 98 |
| 18 | trans-(Rs,2S,3S)-3e | H (R-1e) | H (2a) | 55 | 56 : 44 | 98 |
| 19 | trans-(Rs,2S,3S)-3f | 5-Cl (R-1b) | 4-Cl (2b) | 69 | 74 : 26 | 98 |
| 20 | trans-(Rs,2S,3S)-3g | 5-Br (R-1c) | 4-Cl (2b) | 55 | 70 : 30 | 98 |
| 21 | trans-(Rs,2S,3S)-3h | 3,5-Cl (R-1d) | 4-Cl (2b) | 51 | 61 : 39 | 92 |
| 22f | trans-(Rs,2S,3S)-3i | H (R-1e) | 4-Cl (2b) | 49 | 63 : 37 | 90 |
| 23f | trans-(Rs,2S,3S)-3j | H (R-1e) | 4-Me (2c) | 72 | 73 : 27 | 98 |
| 24 | trans-(Rs,2S,3S)-3l | 5-Cl (R-1b) | 4-Me (2c) | 62 | 72 : 28 | 98 |
| 25 | trans-(Rs,2S,3S)-3n | 5-Br (R-1c) | 4-Me (2c) | 63 | 64 : 36 | 98 |
a
Reaction conditions: N-tert-butylsulfinyl imines 1 (0.20 mmol), sulfur ylide 2 (0.50 mmol), in 2 mL of MeCN at 30 °C in the presence of 250 mol % of K3PO4·3H2O.
b
The suffix R or S in the numbering refers to the absolute configuration of the sulfinylimine auxiliary.
c
Isolated yield after silica gel chromatography of 3. trans and cis adducts have been separated by column chromatography and that only the major trans-adducts are described.
d
Cis/trans ratio determined from the 1H NMR of the crude reaction mixture.
e
De determined from 1H NMR of the crude reaction mixture.
f
N-tert-Butyl sulfinyl imine of β-naphthylaldehyde was used.