The catalytic asymmetric diels-alder reactions and post-cycloaddition reductive transpositions of 1-hydrazinodienes

Hao Xie; Glenn M. Sammis; Eric M. Flamme; Christina M. Kraml; Erik J. Sorensen

doi:10.1002/chem.201102394

The catalytic asymmetric diels-alder reactions and post-cycloaddition reductive transpositions of 1-hydrazinodienes

Hao Xie, Glenn M. Sammis, Eric M. Flamme, Christina M. Kraml, Erik J. Sorensen

Chemistry

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

12 Scopus citations

Abstract

Cycling through: Type I cyclohexenes are produced with high margins of stereoselectivity by chiral, catalyst-controlled, Diels-Alder reactions between 1-hydrazinodienes and N-acryloyl oxazolidinone dienophiles, and readily transformed to cyclohexenes III via a putative, transient allylic diazene II (see scheme). This chemistry gives access to functionalized cyclohexenes that can be difficult to construct by alternative methods.

Original language	English (US)
Pages (from-to)	11131-11134
Number of pages	4
Journal	Chemistry - A European Journal
Volume	17
Issue number	40
DOIs	https://doi.org/10.1002/chem.201102394
State	Published - Sep 26 2011

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis
Organic Chemistry

Keywords

asymmetric Diels-Alder reaction
cyclization
cycloaddition
hydrazinodienes
sigmatropic rearrangement

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10.1002/chem.201102394

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abstract = "Cycling through: Type I cyclohexenes are produced with high margins of stereoselectivity by chiral, catalyst-controlled, Diels-Alder reactions between 1-hydrazinodienes and N-acryloyl oxazolidinone dienophiles, and readily transformed to cyclohexenes III via a putative, transient allylic diazene II (see scheme). This chemistry gives access to functionalized cyclohexenes that can be difficult to construct by alternative methods.",

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T1 - The catalytic asymmetric diels-alder reactions and post-cycloaddition reductive transpositions of 1-hydrazinodienes

AU - Xie, Hao

AU - Sammis, Glenn M.

AU - Flamme, Eric M.

AU - Kraml, Christina M.

AU - Sorensen, Erik J.

PY - 2011/9/26

Y1 - 2011/9/26

N2 - Cycling through: Type I cyclohexenes are produced with high margins of stereoselectivity by chiral, catalyst-controlled, Diels-Alder reactions between 1-hydrazinodienes and N-acryloyl oxazolidinone dienophiles, and readily transformed to cyclohexenes III via a putative, transient allylic diazene II (see scheme). This chemistry gives access to functionalized cyclohexenes that can be difficult to construct by alternative methods.

AB - Cycling through: Type I cyclohexenes are produced with high margins of stereoselectivity by chiral, catalyst-controlled, Diels-Alder reactions between 1-hydrazinodienes and N-acryloyl oxazolidinone dienophiles, and readily transformed to cyclohexenes III via a putative, transient allylic diazene II (see scheme). This chemistry gives access to functionalized cyclohexenes that can be difficult to construct by alternative methods.

KW - asymmetric Diels-Alder reaction

KW - cyclization

KW - cycloaddition

KW - hydrazinodienes

KW - sigmatropic rearrangement

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JO - Chemistry - A European Journal

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The catalytic asymmetric diels-alder reactions and post-cycloaddition reductive transpositions of 1-hydrazinodienes

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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