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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.