Asymmetric Cyclopropanation and Epoxidation via a Catalytically Formed Chiral Auxiliary

ChemInform Abstract: The Use of 1,2-trans-Cyclohexanediol as an Efficient Chiral Auxiliary for the Asymmetric Cyclopropanation of Allylic Ethers.

ChemInform ◽

10.1002/chin.199418028 ◽

2010 ◽

Vol 25 (18) ◽

pp. no-no

Author(s):

A. B. CHARETTE ◽

J.-F. MARCOUX

Keyword(s):

Chiral Auxiliary ◽

Asymmetric Cyclopropanation ◽

Allylic Ethers

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The use of 1,2-O-isopropylidene-α-d-xylofuranose as a chiral auxiliary in asymmetric cyclopropanation reactions

Tetrahedron Asymmetry ◽

10.1016/j.tetasy.2009.02.062 ◽

2009 ◽

Vol 20 (9) ◽

pp. 1065-1072 ◽

Cited By ~ 15

Author(s):

José M. Vega-Pérez ◽

Ignacio Periñán ◽

Fernando Iglesias-Guerra

Keyword(s):

Chiral Auxiliary ◽

Asymmetric Cyclopropanation

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ChemInform Abstract: Asymmetric Cyclopropanation of Allylic Ethers: Cleavage and Regeneration of the Chiral Auxiliary.

ChemInform ◽

10.1002/chin.199404046 ◽

2010 ◽

Vol 25 (4) ◽

pp. no-no

Author(s):

A. B. CHARETTE ◽

B. COTE

Keyword(s):

Chiral Auxiliary ◽

Asymmetric Cyclopropanation ◽

Allylic Ethers

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ChemInform Abstract: Asymmetric Cyclopropanation Using Amino Acid as Chiral Auxiliary.

ChemInform ◽

10.1002/chin.200924198 ◽

2009 ◽

Vol 40 (24) ◽

Author(s):

Debarati Mitra ◽

Arjun Sengupta ◽

Kumar Biradha ◽

Amit Basak

Keyword(s):

Amino Acid ◽

Chiral Auxiliary ◽

Asymmetric Cyclopropanation

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The use of 1,2-trans-cyclohexanediol as an efficient chiral auxiliary for the asymmetric cyclopropanation of allylic ethers

Tetrahedron Letters ◽

10.1016/s0040-4039(00)79275-6 ◽

1993 ◽

Vol 34 (45) ◽

pp. 7157-7160 ◽

Cited By ~ 22

Author(s):

André B. Charette ◽

Jean-François Marcoux

Keyword(s):

Chiral Auxiliary ◽

Asymmetric Cyclopropanation ◽

Allylic Ethers

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ChemInform Abstract: The Use of 1,2-O-Isopropylidene-α-D-xylofuranose as a Chiral Auxiliary in Asymmetric Cyclopropanation Reactions.

ChemInform ◽

10.1002/chin.200942025 ◽

2009 ◽

Vol 40 (42) ◽

Author(s):

Jose M. Vega-Perez ◽

Ignacio Perinan ◽

Fernando Iglesias-Guerra

Keyword(s):

Chiral Auxiliary ◽

Asymmetric Cyclopropanation

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Asymmetric cyclopropanation of allylic ethers: cleavage and regeneration of the chiral auxiliary

The Journal of Organic Chemistry ◽

10.1021/jo00056a028 ◽

1993 ◽

Vol 58 (4) ◽

pp. 933-936 ◽

Cited By ~ 44

Author(s):

Andre B. Charette ◽

Bernard Cote

Keyword(s):

Chiral Auxiliary ◽

Asymmetric Cyclopropanation ◽

Allylic Ethers

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Asymmetric cyclopropanation using amino acid as chiral auxiliary

Tetrahedron Asymmetry ◽

10.1016/j.tetasy.2008.11.009 ◽

2008 ◽

Vol 19 (23) ◽

pp. 2678-2681 ◽

Cited By ~ 7

Author(s):

Debarati Mitra ◽

Arjun Sengupta ◽

Kumar Biradha ◽

Amit Basak

Keyword(s):

Amino Acid ◽

Chiral Auxiliary ◽

Asymmetric Cyclopropanation

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Asymmetric Cyclopropanation and Epoxidation via a Catalytically Formed Chiral Auxiliary

Angewandte Chemie International Edition ◽

10.1002/anie.202113925 ◽

2022 ◽

Author(s):

Mikus Purins ◽

Jerome Waser

Keyword(s):

Chiral Auxiliary ◽

Asymmetric Cyclopropanation

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Role of Additives to Overcome Limitations of Intermolecular Rhodium-Catalyzed Asymmetric Cyclopropanation

10.26434/chemrxiv.14479593.v1 ◽

2021 ◽

Author(s):

Jack C. Sharland ◽

Bo Wei ◽

David J. Hardee ◽

Timothy R Hodges ◽

Wei Gong ◽

...

Keyword(s):

Chiral Auxiliary ◽

Asymmetric Induction ◽

Asymmetric Cyclopropanation ◽

Enantioselective Syntheses

This study describes general methods for the enantioselective syntheses of disubstituted cyclopropane carboxylates including substitution patterns or heterocycle functionality previously observed as significant limitations. The key step is the dirhodium tetracarboxylate-catalyzed asymmetric cyclopropanation of vinyl arenes with aryl- or heteroaryldiazoacetates. The reactions are highly diastereoselective and high asymmetric induction could be achieved using either (<i>R</i>)-pantolactone as a chiral auxiliary or chiral dirhodium tetracarboxylate catalysts.

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