Iterative Coupling of Two Different Enones by Nitromethane Using Bifunctional Thiourea Organocatalysts. Stereocontrolled Assembly of Cyclic and Acyclic Structures

Szilárd Varga, Gergely Jakab, A. Csámpai, T. Soós

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

An organocatalytic iterative assembly line has been developed in which nitromethane was sequentially coupled with two different enones using a combination of pseudoenantiomeric cinchona-based thiourea catalysts. Application of unsaturated aldehydes and ketones in the second step of the iterative sequence allows the construction of cyclic syn-ketols and acyclic compounds with multiple contiguous stereocenters. The combination of the multifunctional substrates and ambident electrophiles rendered some organocatalytic transformations possible that have not yet been realized in bifunctional noncovalent organocatalysis.

Original languageEnglish
Pages (from-to)8990-8996
Number of pages7
JournalJournal of Organic Chemistry
Volume80
Issue number18
DOIs
Publication statusPublished - Sep 18 2015

Fingerprint

Cinchona
Thiourea
Ketones
Aldehydes
Catalysts
Substrates
nitromethane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

@article{f7e3ad62fc5c48da9ca22039751122e6,
title = "Iterative Coupling of Two Different Enones by Nitromethane Using Bifunctional Thiourea Organocatalysts. Stereocontrolled Assembly of Cyclic and Acyclic Structures",
abstract = "An organocatalytic iterative assembly line has been developed in which nitromethane was sequentially coupled with two different enones using a combination of pseudoenantiomeric cinchona-based thiourea catalysts. Application of unsaturated aldehydes and ketones in the second step of the iterative sequence allows the construction of cyclic syn-ketols and acyclic compounds with multiple contiguous stereocenters. The combination of the multifunctional substrates and ambident electrophiles rendered some organocatalytic transformations possible that have not yet been realized in bifunctional noncovalent organocatalysis.",
author = "Szil{\'a}rd Varga and Gergely Jakab and A. Cs{\'a}mpai and T. So{\'o}s",
year = "2015",
month = "9",
day = "18",
doi = "10.1021/acs.joc.5b01474",
language = "English",
volume = "80",
pages = "8990--8996",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "18",

}

TY - JOUR

T1 - Iterative Coupling of Two Different Enones by Nitromethane Using Bifunctional Thiourea Organocatalysts. Stereocontrolled Assembly of Cyclic and Acyclic Structures

AU - Varga, Szilárd

AU - Jakab, Gergely

AU - Csámpai, A.

AU - Soós, T.

PY - 2015/9/18

Y1 - 2015/9/18

N2 - An organocatalytic iterative assembly line has been developed in which nitromethane was sequentially coupled with two different enones using a combination of pseudoenantiomeric cinchona-based thiourea catalysts. Application of unsaturated aldehydes and ketones in the second step of the iterative sequence allows the construction of cyclic syn-ketols and acyclic compounds with multiple contiguous stereocenters. The combination of the multifunctional substrates and ambident electrophiles rendered some organocatalytic transformations possible that have not yet been realized in bifunctional noncovalent organocatalysis.

AB - An organocatalytic iterative assembly line has been developed in which nitromethane was sequentially coupled with two different enones using a combination of pseudoenantiomeric cinchona-based thiourea catalysts. Application of unsaturated aldehydes and ketones in the second step of the iterative sequence allows the construction of cyclic syn-ketols and acyclic compounds with multiple contiguous stereocenters. The combination of the multifunctional substrates and ambident electrophiles rendered some organocatalytic transformations possible that have not yet been realized in bifunctional noncovalent organocatalysis.

UR - http://www.scopus.com/inward/record.url?scp=84941921452&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84941921452&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.5b01474

DO - 10.1021/acs.joc.5b01474

M3 - Article

AN - SCOPUS:84941921452

VL - 80

SP - 8990

EP - 8996

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 18

ER -