RT info:eu-repo/semantics/article
T1 Dimethylzinc-mediated enantioselective addition of terminal alkynes to 1,2-diketones using perhydro-1,3-benzoxazines as ligands
A1 Prieto, Elena
A1 Infante, Rebeca
A1 Nieto Román, Francisco Javier
A1 Andrés Juan, Celia
K1 Catálisis enantioselectiva, compuestos organozíncicos, 1,2-dicetonas, alfa-alquinil-alfa-hidroxicetonas
K1 2306.99 Química Orgánica-Síntesis enantioselectiva
AB A conformationally restricted perhydro-1,3-benzoxazine derived from (−)-8-aminomenthol behaves as agood chiral ligand in the dimethylzinc-mediated enantioselective monoaddition of aromatic and aliphaticterminal alkynes to 1,2-diketones. The corresponding α-hydroxyketones were obtained in good yieldswith high enantioselectivities starting from both aromatic and aliphatic 1,2-diketones. The alkynylation ofunsymmetrical 1,2-diketones with electronically different substituents also proceeds with high regio- andenantioselectivity. This reaction provides a practical method to synthesize ketones bearing a chiral tertiarypropargylic alcohol.
PB The Royal Society of Chemistry
SN 1477-0520
YR 2021
FD 2021
LK https://uvadoc.uva.es/handle/10324/63062
UL https://uvadoc.uva.es/handle/10324/63062
LA eng
NO Organic and Biomolecular. Chemistry, 2021, vol. 19, n 17, p 3859-3867
NO Producción Científica
DS UVaDOC
RD 22-nov-2024