Stereoselective Thio-Michael/Aldol Tandem Reaction to α,β-Unsaturated Esters
✍ Scribed by Kamimura, Akio; Mitsudera, Hiromasa; Asano, Shigeru; Kidera, Seiji; Kakehi, Akikazu
- Book ID
- 126969657
- Publisher
- American Chemical Society
- Year
- 1999
- Tongue
- English
- Weight
- 117 KB
- Volume
- 64
- Category
- Article
- ISSN
- 0022-3263
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📜 SIMILAR VOLUMES
Under a proper reaction condition, simple ester enolates add to d,e-unsaturated esters highly stereoselectively to give erythro or threoglutarates. Previously, we have shown that lithium enolates derived from simple monoesters react with fi,p-unsaturated esters to give glutarates in high yiela. 1)
The reaction of to-oxo-(x,13-unsaturated esters with lithium thiolates afforded the Michael-aldol tandem cyclization products in good to perfect stereoselectivity depending on the nature of thiolates.