The First Asymmetric Carroll Rearrangement Diastereo‐ and Enantioselective Synthesis of Polyfunctional Ketones with Vicinal Quaternary and Tertiary Stereogenic Centers | Zendy

Enders Dieter | Zendy; Knopp Monika | Zendy; Runsink Jan | Zendy; Raabe Gerhard | Zendy

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The First Asymmetric Carroll Rearrangement Diastereo‐ and Enantioselective Synthesis of Polyfunctional Ketones with Vicinal Quaternary and Tertiary Stereogenic Centers

Author(s) -

Enders Dieter,

Knopp Monika,

Runsink Jan,

Raabe Gerhard

Publication year - 1996

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199619960708

Subject(s) - stereocenter , vicinal , enantioselective synthesis , chemistry , stereochemistry , enantiomer , sigmatropic reaction , organic chemistry , catalysis

The first asymmetric Carroll rearrangement opens up an efficient access to highly functionalised ketones 4 and 7 with vicinal quaternary and tertiary stereogenic centres of excellent diastereo‐ and enantiomeric purity ( de =89–96%, ee =82 to >98%) by using the SAMP/RAMP hydrazone methodology. Starting from hydrazones ( S )‐ 2 , we describe a dianionic and a Lewis acid‐mediated variant of the [3.3]‐sigmatropic Carroll rearrangement. The relative and absolute configuration of the new stereogenic centres created by C–C bond formation were assigned by X‐ray crystallographic analysis of the hydrazones 3h and 3j .

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