Diels‐Alder Reaction of Racemic β1‐Isopropyl‐α1‐methylene‐β1‐lactone with Enantiomerically Pure 5,6,7,7a‐Tetrahydro‐7a‐methyl‐1‐phenyl‐4 H 1‐indene and Retro Cleavage of the Resulting Spiro‐β1‐lactones: The First Case of a Perfect Topological Resolution | Zendy

Adam Waldemar | Zendy; Nava Salgado Victor O. | Zendy; Wegener Bernd | Zendy; Winterfeldt Ekkehard | Zendy

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Diels‐Alder Reaction of Racemic β1‐Isopropyl‐α1‐methylene‐β1‐lactone with Enantiomerically Pure 5,6,7,7a‐Tetrahydro‐7a‐methyl‐1‐phenyl‐4 H 1‐indene and Retro Cleavage of the Resulting Spiro‐β1‐lactones: The First Case of a Perfect Topological Resolution

Author(s) -

Adam Waldemar,

Nava Salgado Victor O.,

Wegener Bernd,

Winterfeldt Ekkehard

Publication year - 1993

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19931260638

Subject(s) - chemistry , cyclopentadiene , cycloaddition , lactone , isopropyl , indene , adduct , methylene , enantiomer , diels–alder reaction , cleavage (geology) , stereochemistry , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering

The racemic β1‐isopropyl‐α1‐methylene‐β1‐lactone 1 undergoes a configuration‐dependent, highly selective [4 + 2] cycloaddition to the enantiomerically pure cyclopentadiene 2 ; chromatographic separation of the adducts and subsequent thermal retro cleavage provide the pure enantiomers ( S )‐ 1 and ( R )‐ 1 in 99% e.e.

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