✦ LIBER ✦
ChemInform Abstract: Hydroxyl- versus Amide-Directed Cyclopropanation from the Allylic Position in 1-Hydroxy-4-N-acyl-cyclopentenes under Modified Simmons- Smith Conditions.
✍ Scribed by P. RUSS; A. EZZITOUNI; V. E. MARQUEZ
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 30 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Hydroxyl-versus Amide-Directed Cyclopropanation from the Allylic Position in 1-Hydroxy-4-N-acyl-cyclopentenes under Modified Simmons-Smith Conditions.
-It is clearly demonstrated that the Ac group of the title cyclopentenes (III) and (VI) exerts a stronger diastereofacial directing effect than the OH-functionality in the title reaction. These results are complement to a published diazomethane/Pd(OAc)2 protocol in which the methylene moiety is introduced anti to an allylic NH-Ac group. -(RUSS, P.;