Abstract
The reaction of allyltributyltin with methyl 2-[N-((4S)-4-(1-methylethyl)-2-oxazolidinone-3-carbamoyl)amino]-2-bromoacetate (5 a) was accelerated at -50°C in the presence of AIBN and stopped in the presence of galvinoxyl, indicating that the reaction proceeds through a radical mechanism. The reaction was accelerated dramatically at -78°C in the presence of ZnCl2·OEt2, and the ZnCl2-mediated reaction was stopped in the presence of galvinoxyl. In the presence of 2 equiv ZnCl2·OEt2, the reaction afforded methyl (2R)-2-[N-((4SH-(1-methylethyl)-2-oxazolidinone-3-carbamoyl)amino]-4-pentenoate {6a(R)} with high diastereoselectivity (93:7). Taken together, ZnCl2·OEt2 works as a radical initiator as well as chelating agent.
| Original language | English |
|---|---|
| Pages (from-to) | 765-780 |
| Number of pages | 16 |
| Journal | Heterocycles |
| Volume | 47 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - 1998 Jan 1 |
ASJC Scopus subject areas
- Analytical Chemistry
- Pharmacology
- Organic Chemistry
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Yamamoto, Y., Onuki, S., Yumoto, M., & Asao, N. (1998). Radical reaction initiated and stereocontrolled by zinc chloride. Heterocycles, 47(2), 765-780. https://doi.org/10.3987/COM-97-S(N)71