Premium
Enantioselective Organocatalytic Synthesis of α‐Cyclopropylphosphonates through a Domino Michael Addition/Intramolecular Alkylation Reaction
Author(s) -
Faísca Phillips Ana Maria,
Barros Maria Teresa
Publication year - 2014
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.201301207
Subject(s) - enantioselective synthesis , chemistry , domino , michael reaction , intramolecular force , alkylation , organocatalysis , cascade reaction , combinatorial chemistry , organic chemistry , catalysis
An organocatalytic domino reaction consisting of Michael addition/intramolecular alkylation between α,β‐unsaturated aldehydes and bromophosphonoacetates was developed. Highly functionalised cyclopropylphosphonates containing three chiral centres, one of them quaternary, were obtained with good diastereoselectivities of up to 83:17 and very high enantioselectivities of up to 99 %.