Enantioselective Organocatalytic Synthesis of α-Cyclopropylphosphonates through a Domino Michael Addition/Intramolecular Alkylation Reaction

Ana Maria Madeira Martins Faísca Phillips; Maria Teresa Barros

doi:10.1002/ejoc.201301207

Enantioselective Organocatalytic Synthesis of α-Cyclopropylphosphonates through a Domino Michael Addition/Intramolecular Alkylation Reaction

Ana Maria Madeira Martins Faísca Phillips, Maria Teresa Barros

Research output: Contribution to journal › Article

6 Citations (Scopus)

Abstract

An organocatalytic domino reaction consisting of Michael addition/intramolecular alkylation between ,-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%.

Original language	English
Pages (from-to)	152-163
Journal	European Journal of Organic Chemistry
Volume	2014
Issue number	1
DOIs	https://doi.org/10.1002/ejoc.201301207
Publication status	Published - 1 Jan 2014

Fingerprint

Keywords

Aldehydes
Cyclopropanes
Domino reactions
Michael addition
Organocatalysis

Cite this

Phillips, A. M. M. M. F., & Barros, M. T. (2014). Enantioselective Organocatalytic Synthesis of α-Cyclopropylphosphonates through a Domino Michael Addition/Intramolecular Alkylation Reaction. European Journal of Organic Chemistry, 2014(1), 152-163. https://doi.org/10.1002/ejoc.201301207

@article{b4f18678123c4f2aaf4c15b2ff2953de,

title = "Enantioselective Organocatalytic Synthesis of α-Cyclopropylphosphonates through a Domino Michael Addition/Intramolecular Alkylation Reaction",

abstract = "An organocatalytic domino reaction consisting of Michael addition/intramolecular alkylation between ,-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{\%}.",

keywords = "Aldehydes , Cyclopropanes , Domino reactions , Michael addition , Organocatalysis",

author = "Phillips, {Ana Maria Madeira Martins Fa{\'i}sca} and Barros, {Maria Teresa}",

note = "SCOPUSID:84890780833 WOS:000328631700018",

year = "2014",

month = "1",

day = "1",

doi = "10.1002/ejoc.201301207",

language = "English",

volume = "2014",

pages = "152--163",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "WILEY-V C H VERLAG GMBH",

number = "1",

}

TY - JOUR

T1 - Enantioselective Organocatalytic Synthesis of α-Cyclopropylphosphonates through a Domino Michael Addition/Intramolecular Alkylation Reaction

AU - Phillips, Ana Maria Madeira Martins Faísca

AU - Barros, Maria Teresa

N1 - SCOPUSID:84890780833 WOS:000328631700018

PY - 2014/1/1

Y1 - 2014/1/1

N2 - An organocatalytic domino reaction consisting of Michael addition/intramolecular alkylation between ,-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%.

AB - An organocatalytic domino reaction consisting of Michael addition/intramolecular alkylation between ,-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%.

KW - Aldehydes

KW - Cyclopropanes

KW - Domino reactions

KW - Michael addition

KW - Organocatalysis

U2 - 10.1002/ejoc.201301207

DO - 10.1002/ejoc.201301207

M3 - Article

VL - 2014

SP - 152

EP - 163

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 1

ER -

Access to Document

10.1002/ejoc.201301207