Organocatalytic synthesis of spirocyclohexane indane-1,3-diones via a chiral squaramide-catalyzed Michael/aldol cascade reaction of γ-nitro ketones and 2-arylideneindane-1,3-diones

Mamatha Amireddy, Kwunmin Chen

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The paper presents an efficient and stereoselective method for constructing spirocyclohexane indane-1,3-diones. This method is based on a chiral squaramide-catalysed highly diastereo- and enantioselective cascade Michael/aldol reaction between γ-nitro ketones and 2-arylidene-1,3-indanedione that affords functionalised spirocyclohexane products in high chemical yields with the formation of three stereogenic centres (57-97%; up to >20:1 dr and 86% ee).

Original languageEnglish
Pages (from-to)8003-8008
Number of pages6
JournalTetrahedron
Volume71
Issue number42
DOIs
Publication statusPublished - 2015 Oct 21

Fingerprint

Ketones
3-hydroxybutanal
squaramide
1,2-indanedione

Keywords

  • 2-Arylideneindane-1 3-diones
  • Cascade reaction
  • Michael-aldol
  • Squaramide-catalyst
  • γ-Nitro ketones

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

@article{f6a59c8324ec46d69db30e7d79b624a3,
title = "Organocatalytic synthesis of spirocyclohexane indane-1,3-diones via a chiral squaramide-catalyzed Michael/aldol cascade reaction of γ-nitro ketones and 2-arylideneindane-1,3-diones",
abstract = "The paper presents an efficient and stereoselective method for constructing spirocyclohexane indane-1,3-diones. This method is based on a chiral squaramide-catalysed highly diastereo- and enantioselective cascade Michael/aldol reaction between γ-nitro ketones and 2-arylidene-1,3-indanedione that affords functionalised spirocyclohexane products in high chemical yields with the formation of three stereogenic centres (57-97{\%}; up to >20:1 dr and 86{\%} ee).",
keywords = "2-Arylideneindane-1 3-diones, Cascade reaction, Michael-aldol, Squaramide-catalyst, γ-Nitro ketones",
author = "Mamatha Amireddy and Kwunmin Chen",
year = "2015",
month = "10",
day = "21",
doi = "10.1016/j.tet.2015.08.061",
language = "English",
volume = "71",
pages = "8003--8008",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "42",

}

TY - JOUR

T1 - Organocatalytic synthesis of spirocyclohexane indane-1,3-diones via a chiral squaramide-catalyzed Michael/aldol cascade reaction of γ-nitro ketones and 2-arylideneindane-1,3-diones

AU - Amireddy, Mamatha

AU - Chen, Kwunmin

PY - 2015/10/21

Y1 - 2015/10/21

N2 - The paper presents an efficient and stereoselective method for constructing spirocyclohexane indane-1,3-diones. This method is based on a chiral squaramide-catalysed highly diastereo- and enantioselective cascade Michael/aldol reaction between γ-nitro ketones and 2-arylidene-1,3-indanedione that affords functionalised spirocyclohexane products in high chemical yields with the formation of three stereogenic centres (57-97%; up to >20:1 dr and 86% ee).

AB - The paper presents an efficient and stereoselective method for constructing spirocyclohexane indane-1,3-diones. This method is based on a chiral squaramide-catalysed highly diastereo- and enantioselective cascade Michael/aldol reaction between γ-nitro ketones and 2-arylidene-1,3-indanedione that affords functionalised spirocyclohexane products in high chemical yields with the formation of three stereogenic centres (57-97%; up to >20:1 dr and 86% ee).

KW - 2-Arylideneindane-1 3-diones

KW - Cascade reaction

KW - Michael-aldol

KW - Squaramide-catalyst

KW - γ-Nitro ketones

UR - http://www.scopus.com/inward/record.url?scp=84952874802&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84952874802&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2015.08.061

DO - 10.1016/j.tet.2015.08.061

M3 - Article

AN - SCOPUS:84952874802

VL - 71

SP - 8003

EP - 8008

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 42

ER -