SELECTIVE SYNTHESIS OF TRANS-ANTI-CIS (TAC) OR CIS-ANTI-TRANS (CAT) TRICYCLES FROM THE TRANSANNULAR DIELS-ALDER OF TTT MACROCYCLIC TRIENES
Soucy, P; Dory, YL; Deslongchamps, P
| HERO ID | 4935908 |
|---|---|
| In Press | No |
| Year | 1994 |
| Title | SELECTIVE SYNTHESIS OF TRANS-ANTI-CIS (TAC) OR CIS-ANTI-TRANS (CAT) TRICYCLES FROM THE TRANSANNULAR DIELS-ALDER OF TTT MACROCYCLIC TRIENES |
| Authors | Soucy, P; Dory, YL; Deslongchamps, P |
| Journal | Bulletin de la Société Chimique de Paris |
| Volume | 131 |
| Issue | 3 |
| Page Numbers | 271-278 |
| Abstract | The synthesis and transannular Diels-Alder reactions of trans-trans-trans (TTT) macrocyclic trienes 16 and 26 containing a dimethyl malonate and a monomethyl ester are reported. Compound 16 yields a mixture of two trans-anti-cis (TAC), (27, 73% and 28, 19%) and one cis-anti-trans (CAT) tricycle (29, 8%). Macrocycle 26 gives one TAC (31, 17%) and two CAT tricycles (33, 78% and 34, 5%). These results are explained by considering steric effects in competing chair-boat-chair and chair-boat-boat transition states. |
| Wosid | WOS:A1994NF80600004 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | STEREOCONTROLLED SYNTHESIS; MACROCYCLES; TRICYCLES; TRANSANNULAR DIELS-ALDER REACTION; CYCLOADDITION |