Synthesis of Vicinal -Amino Alcohols from --Butanesulfinyl Aldimines and Cyclopropanols

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2024 Apr 13

PMID 38613513

Authors

Sandra Hernandez-Ibanez

Juan F Ortuno

Ana Sirvent

Carmen Najera

Jose Miguel Sansano

Miguel Yus

Francisco Foubelo

Affiliations

Soon will be listed here.

Abstract

The stereoselective synthesis of vicinal amino alcohols derivatives from 1-substituted cyclopropanols and chiral --butanesulfinyl imines is described. Cyclopropanols are easily prepared from carboxylic esters upon reaction with ethylmagnesium bromide in the presence of titanium tetraisopropoxide and undergo carbon-carbon bond cleavage by means of diethylzinc to produce, upon base deprotonation, enolized zinc homoenolates, which react with chiral sulfinyl imines in a highly regio- and stereoselective manner.

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