Inversion of the Direction of Stereoinduction in the Coupling of Chiral γ,δ-Unsaturated Fischer Carbene Complexes with o-Ethynylbenzaldehyde

A variety of γ,δ-unsaturated carbene complexes that feature a stereogenic center at the β-carbon couple with 2-ethynylbenzaldehyde to afford hydrophenanthrene derivatives with a high degree of stereoinduction. The direction of stereoinduction is opposite for examples where the stereogenic center is...

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Bibliographic Details
Published in:Organic letters 2002-06, Vol.4 (13), p.2121-2124
Main Authors: Ghorai, Binay K, Menon, Suneetha, Johnson, Dennis Lee, Herndon, James W
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Benzaldehydes - chemistry
Hydrocarbons
Kinetics
Methane - analogs & derivatives
Methane - chemistry
Models, Molecular
Stereoisomerism
Steroids - chemical synthesis
Steroids - chemistry
Thermodynamics
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Summary:A variety of γ,δ-unsaturated carbene complexes that feature a stereogenic center at the β-carbon couple with 2-ethynylbenzaldehyde to afford hydrophenanthrene derivatives with a high degree of stereoinduction. The direction of stereoinduction is opposite for examples where the stereogenic center is acyclic vs examples where it is within a ring.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol025808y