Asymmetric Synthesis of 3-Substituted 2-exo-Methylenecyclohexanones via 1,5-Diastereoselection by Using a Chiral Amine

DOI: 10.1021/jo00289a003

Source and publish data:

Journal of Organic Chemistry p. 408 - 410 (1990)

Update date:2022-08-05

Topics:

Authors:

Tamura, Rui

Watabe, Ken-ichiro

Katayama, Hitoshi

Suzuki, Hitomi

Yamamoto, Yukio

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Article abstract of DOI:10.1021/jo00289a003

(S)-2-((2-(Methoxymethyl)-1-pyrrolidinyl)methyl)-2-cyclohexen-1-one (2) underwent asymmetric conjugate addition of R2CuLi in the presence of ZnBr2, followed by elimination of the chiral auxiliary pyrrolidine, to produce the optically active 3-substituted 2-exo-methylenecyclohexanones (3) in 90percent ee.

Full text of DOI:10.1021/jo00289a003

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