Premium
Highly Efficient and Stereoselective Radical Addition of Tertiary Amines to Electron‐Deficient Alkenes − Application to the Enantioselective Synthesis of Necine Bases
Author(s) -
Bertrand Samuel,
Hoffmann Norbert,
Pete JeanPierre
Publication year - 2000
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 - 10.1002/1099-0690(200006)2000:12<2227::aid-ejoc2227>3.0.co;2-8
Subject(s) - chemistry , alkene , stereoselectivity , enantioselective synthesis , radical , selectivity , tertiary amine , electron transfer , radical cyclization , addition reaction , medicinal chemistry , stereochemistry , organic chemistry , catalysis
A convenient and highly efficient method for the regio‐ and stereoselective addition of tertiary amines to electron‐deficient alkenes has been elaborated. It is based on a radical chain reaction of α‐aminyl radicals with alkenes, induced by a photoelectron transfer process between tertiary amines 2a − j and excited electron donor substituted phenyl ketones. The influence of the nature of the amino substituents and of the alkene on the reaction have been examined. In the presence of (5 R )‐5‐menthyloxy‐2‐(5 H )‐furanone ( 1 ) as electron‐deficient alkene, the addition of N ‐alkylpyrrolidines 2a − e occurred with a complete facial selectivity and up to 94% isolated yields. This method has been applied to a fast, efficient and enantioselective synthesis of necine bases.