Enantioselective Organocatalytic Synthesis of α‐Cyclopropylphosphonates through a Domino Michael Addition/Intramolecular Alkylation Reaction | Zendy

Faísca Phillips Ana Maria | Zendy; Barros Maria Teresa | Zendy

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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 %.

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