Lead-Mediated Highly Diastereoselective Allylation of Aldehydes with Cyclic Allylic Halides.
J Org Chem
; 84(9): 5348-5356, 2019 May 03.
Article
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| MEDLINE
| ID: mdl-30977647
ABSTRACT
Lead was found to efficiently mediate the allylation reactions of carbonyl compounds with cyclic allylic halides in the presence of stoichiometric amounts of lithium chloride and a catalytic amount of GaCl3 (20 mol %), leading to the desired homoallylic alcohols in modest to high yields with excellent diastereocontrol (>991 syn/anti) and good functional group tolerance. In contrast, the use of either 2-pyridinecarboxaldehyde as the carbonyl substrate or ( E)-cinnamyl bromide as the allylating agent produced the corresponding product with reversed diastereoselectivity (>991 anti/syn).
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1
Colección:
01-internacional
Banco de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Año:
2019
Tipo del documento:
Article
País de afiliación:
China