✦ LIBER ✦
ChemInform Abstract: Stereochemistry. Part 89. A Highly Stereoselective One-Pot Tandem Consecutive 1,4-Addition-Intramolecular 1,3-Dipolar Cycloaddition Strategy for the Construction of Functionalized Five- and Six-Membered Carbocycles.
✍ Scribed by I. N. N. NAMBOOTHIRI; A. HASSNER; H. E. GOTTLIEB
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 32 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Strategy for the Construction of Functionalized Five-and Six-Membered Carbocycles. -Conjugate addition of the Grignard reagents (II) and (IV) to the nitro olefins (I) leads to the intermediate formation of nitronates, which are trapped as silyl nitronates and subsequently cyclized by intramolecular 1,3-dipolar cycloaddition. The resulting N-(silyloxy) isoxazolidines are readily converted into the corresponding isoxazolines (III), (V), and (VI), completing the entire sequence in one pot. -(NAMBOOTHIRI, I. N.