An N-heterocyclic carbene/lewis acid strategy for the stereoselective synthesis of spirooxindole lactones

Julien Dugal-Tessier; Elizabeth A. O'Bryan; Thomas B.H. Schroeder; Daniel T. Cohen; Karl A. Scheidt

doi:10.1002/anie.201201643

An N-heterocyclic carbene/lewis acid strategy for the stereoselective synthesis of spirooxindole lactones

Julien Dugal-Tessier^*, Elizabeth A. O'Bryan, Thomas B.H. Schroeder, Daniel T. Cohen, Karl A. Scheidt

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

250 Scopus citations

Abstract

A cooperative catalysis approach for the enantioselective formal [3+2] addition of α,β-unsaturated aldehydes to isatins has been developed. Homoenolate annulations of β-aryl enals catalyzed by an N-heterocyclic carbene (NHC) require the addition of lithium chloride for high levels of enantioselectivity. This NHC-catalyzed annulation has been used for the total synthesis of maremycin B.

Original language	English (US)
Pages (from-to)	4963-4967
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	20
DOIs	https://doi.org/10.1002/anie.201201643
State	Published - May 14 2012

Keywords

Lewis acids
asymmetric synthesis
homoenolates
homogeneous catalysis
total synthesis

ASJC Scopus subject areas

General Chemistry
Catalysis

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10.1002/anie.201201643

Cite this

@article{0428c46b39f5450c85a589edb8e7f886,

title = "An N-heterocyclic carbene/lewis acid strategy for the stereoselective synthesis of spirooxindole lactones",

abstract = "A cooperative catalysis approach for the enantioselective formal [3+2] addition of α,β-unsaturated aldehydes to isatins has been developed. Homoenolate annulations of β-aryl enals catalyzed by an N-heterocyclic carbene (NHC) require the addition of lithium chloride for high levels of enantioselectivity. This NHC-catalyzed annulation has been used for the total synthesis of maremycin B.",

keywords = "Lewis acids, asymmetric synthesis, homoenolates, homogeneous catalysis, total synthesis",

author = "Julien Dugal-Tessier and O'Bryan, {Elizabeth A.} and Schroeder, {Thomas B.H.} and Cohen, {Daniel T.} and Scheidt, {Karl A.}",

year = "2012",

month = may,

day = "14",

doi = "10.1002/anie.201201643",

language = "English (US)",

volume = "51",

pages = "4963--4967",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "20",

}

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T1 - An N-heterocyclic carbene/lewis acid strategy for the stereoselective synthesis of spirooxindole lactones

AU - Dugal-Tessier, Julien

AU - O'Bryan, Elizabeth A.

AU - Schroeder, Thomas B.H.

AU - Cohen, Daniel T.

AU - Scheidt, Karl A.

PY - 2012/5/14

Y1 - 2012/5/14

N2 - A cooperative catalysis approach for the enantioselective formal [3+2] addition of α,β-unsaturated aldehydes to isatins has been developed. Homoenolate annulations of β-aryl enals catalyzed by an N-heterocyclic carbene (NHC) require the addition of lithium chloride for high levels of enantioselectivity. This NHC-catalyzed annulation has been used for the total synthesis of maremycin B.

AB - A cooperative catalysis approach for the enantioselective formal [3+2] addition of α,β-unsaturated aldehydes to isatins has been developed. Homoenolate annulations of β-aryl enals catalyzed by an N-heterocyclic carbene (NHC) require the addition of lithium chloride for high levels of enantioselectivity. This NHC-catalyzed annulation has been used for the total synthesis of maremycin B.

KW - Lewis acids

KW - asymmetric synthesis

KW - homoenolates

KW - homogeneous catalysis

KW - total synthesis

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DO - 10.1002/anie.201201643

M3 - Article

C2 - 22489096

AN - SCOPUS:84860856816

SN - 1433-7851

VL - 51

SP - 4963

EP - 4967

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 20

ER -

An N-heterocyclic carbene/lewis acid strategy for the stereoselective synthesis of spirooxindole lactones

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 869605: Experimental Crystal Structure Determination

CCDC 869608: Experimental Crystal Structure Determination

CCDC 869606: Experimental Crystal Structure Determination

Cite this

An N-heterocyclic carbene/lewis acid strategy for the stereoselective synthesis of spirooxindole lactones

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 869605: Experimental Crystal Structure Determination

CCDC 869608: Experimental Crystal Structure Determination

CCDC 869606: Experimental Crystal Structure Determination

Cite this