Enantioselective catalytic 1,2-boronate rearrangements.
Science
; 374(6568): 752-757, 2021 Nov 05.
Article
em En
| MEDLINE
| ID: mdl-34735250
ABSTRACT
A strategy that facilitates the construction of a wide variety of trisubstituted stereocenters through a catalytically accessed common chiral intermediate could prove highly enabling for the field of synthetic chemistry. We report the discovery of enantioselective, catalytic 1,2-boronate rearrangements for the synthesis of α-chloro pinacol boronic esters from readily available boronic esters and dichloromethane. The chiral building blocks produced in these reactions can undergo two sequential stereospecific elaborations to generate a wide assortment of trisubstituted stereocenters. The enantioselective reaction is catalyzed by a lithium-isothiourea-boronate complex, which is proposed to promote rearrangement through a duallithium-induced chloride abstraction orchestrated by Lewis basic functionality on the catalyst scaffold.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Ácidos Borônicos
/
Técnicas de Química Sintética
Idioma:
En
Revista:
Science
Ano de publicação:
2021
Tipo de documento:
Article
País de afiliação:
Estados Unidos