The Stereochemistry of Diels-Alder Adduct of 5-Methyl-2-cyclohexene-1-one with Butadiene

Takashi Harayama; Hidetsura Cho; Mitsuaki Ohtani; Yasuo Inubushi

doi:10.1248/cpb.22.2784

The Stereochemistry of Diels-Alder Adduct of 5-Methyl-2-cyclohexene-1-one with Butadiene

Takashi Harayama, Hidetsura Cho, Mitsuaki Ohtani, Yasuo Inubushi

PHA - Molecular Pharmaceutical Science

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

13 Citations (Scopus)

Abstract

The Diels-Alder reaction of 5-methyl-2-cyclohexene-1-one (I) with butadiene was examined. It was concluded that addition of butadiene to the dienophile (I) took place from the opposite side to a secondary methyl side to give initially the cis adduct (IIb), which then epimerizes mostly to the trans derivative (IIa).

Original language	English
Pages (from-to)	2784-2787
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	22
Issue number	12
DOIs	https://doi.org/10.1248/cpb.22.2784
Publication status	Published - 1974

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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abstract = "The Diels-Alder reaction of 5-methyl-2-cyclohexene-1-one (I) with butadiene was examined. It was concluded that addition of butadiene to the dienophile (I) took place from the opposite side to a secondary methyl side to give initially the cis adduct (IIb), which then epimerizes mostly to the trans derivative (IIa).",

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AU - Ohtani, Mitsuaki

AU - Inubushi, Yasuo

PY - 1974

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AB - The Diels-Alder reaction of 5-methyl-2-cyclohexene-1-one (I) with butadiene was examined. It was concluded that addition of butadiene to the dienophile (I) took place from the opposite side to a secondary methyl side to give initially the cis adduct (IIb), which then epimerizes mostly to the trans derivative (IIa).

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The Stereochemistry of Diels-Alder Adduct of 5-Methyl-2-cyclohexene-1-one with Butadiene

Abstract

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