Design, synthesis, and reactivity of 1-hydrazinodienes for use in organic synthesis

Glenn M. Sammis; Eric M. Flamme; Hao Xie; Douglas M. Ho; Erik J. Sorensen

doi:10.1021/ja052383c

Design, synthesis, and reactivity of 1-hydrazinodienes for use in organic synthesis

Glenn M. Sammis, Eric M. Flamme, Hao Xie, Douglas M. Ho, Erik J. Sorensen

Chemistry

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

30 Scopus citations

Abstract

A new 1-hydrazinodiene (1) has been developed and utilized in Lewis acid catalyzed, intermolecular Diels-Alder reactions with various electron-deficient alkenes. The hydrazine can then be deprotected, and a molecule of methanesulfinic acid is eliminated to provide a putative diazene intermediate (4), which then spontaneously undergoes a suprafacial 1,5-sigmatropic shift to yield stereochemically complex cyclohexenes. This method has been applied to the synthesis of a constitutionally and stereochemically complex decalin derivative.

Original language	English (US)
Pages (from-to)	8612-8613
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	127
Issue number	24
DOIs	https://doi.org/10.1021/ja052383c
State	Published - Jun 22 2005

All Science Journal Classification (ASJC) codes

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

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abstract = "A new 1-hydrazinodiene (1) has been developed and utilized in Lewis acid catalyzed, intermolecular Diels-Alder reactions with various electron-deficient alkenes. The hydrazine can then be deprotected, and a molecule of methanesulfinic acid is eliminated to provide a putative diazene intermediate (4), which then spontaneously undergoes a suprafacial 1,5-sigmatropic shift to yield stereochemically complex cyclohexenes. This method has been applied to the synthesis of a constitutionally and stereochemically complex decalin derivative.",

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AU - Sammis, Glenn M.

AU - Flamme, Eric M.

AU - Xie, Hao

AU - Ho, Douglas M.

AU - Sorensen, Erik J.

PY - 2005/6/22

Y1 - 2005/6/22

N2 - A new 1-hydrazinodiene (1) has been developed and utilized in Lewis acid catalyzed, intermolecular Diels-Alder reactions with various electron-deficient alkenes. The hydrazine can then be deprotected, and a molecule of methanesulfinic acid is eliminated to provide a putative diazene intermediate (4), which then spontaneously undergoes a suprafacial 1,5-sigmatropic shift to yield stereochemically complex cyclohexenes. This method has been applied to the synthesis of a constitutionally and stereochemically complex decalin derivative.

AB - A new 1-hydrazinodiene (1) has been developed and utilized in Lewis acid catalyzed, intermolecular Diels-Alder reactions with various electron-deficient alkenes. The hydrazine can then be deprotected, and a molecule of methanesulfinic acid is eliminated to provide a putative diazene intermediate (4), which then spontaneously undergoes a suprafacial 1,5-sigmatropic shift to yield stereochemically complex cyclohexenes. This method has been applied to the synthesis of a constitutionally and stereochemically complex decalin derivative.

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Design, synthesis, and reactivity of 1-hydrazinodienes for use in organic synthesis

Abstract

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