Organocatalytic Mukaiyama Mannich Reactions of 2,5-Bis(trimethylsilyloxy)furan
Laws, SW; Howard, SY; Mato, R; Meng, S; Fettinger, JC; Shaw, JT
| HERO ID | 5415116 |
|---|---|
| In Press | No |
| Year | 2019 |
| Title | Organocatalytic Mukaiyama Mannich Reactions of 2,5-Bis(trimethylsilyloxy)furan |
| Authors | Laws, SW; Howard, SY; Mato, R; Meng, S; Fettinger, JC; Shaw, JT |
| Journal | Organic Letters |
| Volume | 21 |
| Issue | 13 |
| Page Numbers | 5073-5077 |
| Abstract | The organocatalytic synthesis of densely substituted mono- and bis-γ-lactams involving the Mukaiyama Mannich addition of 2,5-bis(trimethylsilyloxy)furan to imines is described. Use of a ditoluenesulfonylimide catalyst produces γ-lactams from monoaddition, whereas a more acidic catalyst (triflic acid) produces fused bis-lactams from double addition. Optimized organocatalytic conditions allow for the selective synthesis of either desired core as well as the one-pot, multicomponent assembly of the trisubstituted monolactams from aldehydes, amines, and bis-trimethylsilyloxyfuran. An examination of chiral acids found these organocatalysts to be highly active and diastereoselective in the monoaddition reaction, albeit with no enantioselectivity. |
| Doi | 10.1021/acs.orglett.9b01664 |
| Pmid | 31247788 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |