Remote Control of Diastereoselectivity in Intramolecular Reactions of Chiral Allylsilanes
✍ Scribed by Judd, Weston R.; Ban, Sooho; Aubé, Jeffrey
- Book ID
- 126293723
- Publisher
- American Chemical Society
- Year
- 2006
- Tongue
- English
- Weight
- 159 KB
- Volume
- 128
- Category
- Article
- ISSN
- 0002-7863
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📜 SIMILAR VOLUMES
The individual enantiomers of substituted cyclohexyl diazoacetates (I)-(IV) or 2-octyl diazoacetates (V) matched with a configurationally suitable chiral dirhodium(II) carboxamidate catalyst provide an effective methodology for the synthesis of lactones with exceptional diastereoand regiocontrol. Th
The ester-allylsilanes ( 5) and ( 6) and the acid-allylsilane (7) react stereoselectively with m-CPBA; the major product from ( 5) and ( 7) was the y-lactone (4), whereas (6) failed to undergo lactonisation, the major product in this case was the P,wpoxy-silane (12).