Rhodium-catalyzed enantioselective addition to unsymmetrical α-diketones: Tandem one-pot synthesis of optically active 3-tetrasubstituted isochroman derivatives

Ting Shun Zhu, Jianping Chen, Ming Hua Xu

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

The domino effect: An efficient and general catalytic one-pot synthesis of quaternary-substituted isochroman derivatives has been developed (see scheme). The cascade transformation relies on rhodium-catalyzed highly regio- and enantioselective 1,2-addition of arylboronic acids to unsymmetrical α-diketones and intramolecular etherification or esterification, and provides a variety of enantioenriched isochromanones under exceptionally mild conditions.

Original languageEnglish (US)
Pages (from-to)865-869
Number of pages5
JournalChemistry - A European Journal
Volume19
Issue number3
DOIs
StatePublished - Jan 14 2013
Externally publishedYes

Fingerprint

Rhodium
Esterification
Derivatives
Acids

Keywords

  • AC-7954
  • asymmetric catalysis
  • domino reactions
  • isochromans
  • rhodium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

@article{d82dbe39548748e5a609ba55b77bbcae,
title = "Rhodium-catalyzed enantioselective addition to unsymmetrical α-diketones: Tandem one-pot synthesis of optically active 3-tetrasubstituted isochroman derivatives",
abstract = "The domino effect: An efficient and general catalytic one-pot synthesis of quaternary-substituted isochroman derivatives has been developed (see scheme). The cascade transformation relies on rhodium-catalyzed highly regio- and enantioselective 1,2-addition of arylboronic acids to unsymmetrical α-diketones and intramolecular etherification or esterification, and provides a variety of enantioenriched isochromanones under exceptionally mild conditions.",
keywords = "AC-7954, asymmetric catalysis, domino reactions, isochromans, rhodium",
author = "Zhu, {Ting Shun} and Jianping Chen and Xu, {Ming Hua}",
year = "2013",
month = "1",
day = "14",
doi = "10.1002/chem.201203701",
language = "English (US)",
volume = "19",
pages = "865--869",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "3",

}

TY - JOUR

T1 - Rhodium-catalyzed enantioselective addition to unsymmetrical α-diketones

T2 - Tandem one-pot synthesis of optically active 3-tetrasubstituted isochroman derivatives

AU - Zhu, Ting Shun

AU - Chen, Jianping

AU - Xu, Ming Hua

PY - 2013/1/14

Y1 - 2013/1/14

N2 - The domino effect: An efficient and general catalytic one-pot synthesis of quaternary-substituted isochroman derivatives has been developed (see scheme). The cascade transformation relies on rhodium-catalyzed highly regio- and enantioselective 1,2-addition of arylboronic acids to unsymmetrical α-diketones and intramolecular etherification or esterification, and provides a variety of enantioenriched isochromanones under exceptionally mild conditions.

AB - The domino effect: An efficient and general catalytic one-pot synthesis of quaternary-substituted isochroman derivatives has been developed (see scheme). The cascade transformation relies on rhodium-catalyzed highly regio- and enantioselective 1,2-addition of arylboronic acids to unsymmetrical α-diketones and intramolecular etherification or esterification, and provides a variety of enantioenriched isochromanones under exceptionally mild conditions.

KW - AC-7954

KW - asymmetric catalysis

KW - domino reactions

KW - isochromans

KW - rhodium

UR - http://www.scopus.com/inward/record.url?scp=84872179702&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84872179702&partnerID=8YFLogxK

U2 - 10.1002/chem.201203701

DO - 10.1002/chem.201203701

M3 - Article

C2 - 23239222

AN - SCOPUS:84872179702

VL - 19

SP - 865

EP - 869

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 3

ER -