Highly Diastereo‐ and Enantioselective Cascade Synthesis of Bicyclic Lactams in One‐Pot

A versatile and highly stereoselective synthetic route to functionalized bi‐ and tricyclic lactams (up to > 20:1 dr and 99 % ee) in one pot from simple starting materials (allylic alcohols, enals, diamines and amino alcohols) using cascade transformations promoted by chiral amine/Brønsted or meta...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2018-03, Vol.2018 (9), p.1158-1164
Main Authors: Jiang, Yan, Deiana, Luca, Alimohammadzadeh, Rana, Liu, Leifeng, Sun, Junliang, Córdova, Armando
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Aminal
Asymmetric catalysis
Bicyclic lactams
Catalysis
Diamines
Hemiaminal ether
Oxygen
Relay catalysis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A versatile and highly stereoselective synthetic route to functionalized bi‐ and tricyclic lactams (up to > 20:1 dr and 99 % ee) in one pot from simple starting materials (allylic alcohols, enals, diamines and amino alcohols) using cascade transformations promoted by chiral amine/Brønsted or metal/chiral amine/Brønsted relay catalysis is disclosed. Here molecular oxygen is employed as the terminal oxidant for the latter relay catalysis approach. A highly stereoselective synthetic route to functionalized bi‐ and tricyclic lactams (up to >20:1 dr and 99 % ee) in one pot from simple starting materials (allylic alcohols, enals, diamines and amino alcohols) using cascade transformations promoted by combination of 2 or three catalysts is disclosed.
ISSN:1434-193X
1099-0690
1099-0690
DOI:10.1002/ejoc.201701789