Asymmetric Synthesis  of Both Enantiomers of Protected 5‐Hydroxynorvaline by Hetero‐Diels‐Alder Addition of ethyl 2‐Nitrosoacrylate to ( R )‐ and ( S )‐1‐Phenylbutyl Vinyl Ether | Zendy

Massen Zoe S. | Zendy; Gallos John K. | Zendy

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Asymmetric Synthesis of Both Enantiomers of Protected 5‐Hydroxynorvaline by Hetero‐Diels‐Alder Addition of ethyl 2‐Nitrosoacrylate to ( R )‐ and ( S )‐1‐Phenylbutyl Vinyl Ether

Author(s) -

Massen Zoe S.,

Gallos John K.

Publication year - 2012

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.907

Subject(s) - chemistry , enantiomer , ether , diels–alder reaction , vigabatrin , vinyl ether , organic chemistry , catalysis , anticonvulsant , polymer , neuroscience , copolymer , epilepsy , biology

Both enantiomers of protected 5‐hydroxynorvaline were prepared by hetero‐Diels‐Alder addition of ethyl 2‐nitrosoacrylate to readily available ( R )‐ and ( S )‐1‐phenylbutyl vinyl ether and a further three‐step manipulation. Attempted synthesis of (±)‐vigabatrin from protected (±)‐5‐hydroxynorvaline was unsuccessful.

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