期刊
SYNTHESIS-STUTTGART
卷 44, 期 15, 页码 2424-2430出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0031-1290396
关键词
enantioselectivity; Michael addition; cyclization; aminonitroethene; organocatalysis
资金
- European Commission [FP7-201431]
- Slovak Research and Development Agency [DO7RP-0017-08, VVCE 0070/07]
- Slovak State Programme [2003SP200280203]
The organocatalytic addition of substituted oxyacetaldehydes to 2-acylaminonitroethenes proceeded with good to high diastereoselectivities and enantioselectivities. The resulting adducts reacted with ethyl 2-(diethoxyphosphoryl) acrylate to afford highly functionalized cyclohexenes. A thiol-free protocol for cyclization has been developed that leads to a separable mixture of two diaste-reoisomers. The unwanted diastereoisomer can be efficiently epimerized. The resulting cyclohexenes are precursors to oseltamivir and its analogues. The synthesis of the key reagent, 3-pentyloxy-aldehyde, was also improved.
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