Hydroxyl- versus amide-directed cyclopropanation from the allylic position in 1-hydroxy-4-N-acyl-cyclopentenes under modified Simmons-Smith conditions

Autor:	Victor E. Marquez, Abdallah Ezzitouni, Pamela Russ
Rok vydání:	1997
Předmět:	Allylic rearrangement Cyclopropanation Stereochemistry Organic Chemistry food and beverages Diethylzinc Ring (chemistry) Biochemistry chemistry.chemical_compound chemistry Amide Drug Discovery Cyclopentene Methylene
Zdroj:	Tetrahedron Letters. 38:723-726
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(96)02425-2
Popis:	In a functionalized cyclopentene having allylic OH and NH-acyl groups on opposite faces of the ring, the diastereoselective delivery of the incoming methylene group in the diethylzinc version of the Simmons-Smith reaction was completely directed by the NH group. The diastereoselectivity of the reaction can be reversed by complete protection of the amide.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f33429246233b8d6301007ce36d94789 https://doi.org/10.1016/s0040-4039(96)02425-2 Zobrazit plný text záznamu Full Text from ScienceDirect