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Highly Diastereo‐ and Enantioselective Cascade Synthesis of Bicyclic Lactams in One‐Pot
Author(s) -
Jiang Yan,
Deiana Luca,
Alimohammadzadeh Rana,
Liu Leifeng,
Sun Junliang,
Córdova Armando
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701789
Subject(s) - chemistry , enantioselective synthesis , allylic rearrangement , amine gas treating , combinatorial chemistry , catalysis , bicyclic molecule , cascade , stereoselectivity , organocatalysis , cascade reaction , brønsted–lowry acid–base theory , organic chemistry , stereochemistry , chromatography
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.