trans-2-Tritylcyclohexanol as a chiral auxiliary in permanganate-mediated oxidative cyclization of 2-methylenehept-5-enoates: application to the synthesis of trans-(+)-linalool oxide.
Org Lett
; 16(19): 5104-7, 2014 Oct 03.
Article
em En
| MEDLINE
| ID: mdl-25225741
ABSTRACT
The permanganate-mediated oxidative cyclization of a series of 2-methylenehept-5-eneoates bearing different chiral auxiliaries was investigated, leading to the discovery of trans-2-tritylcyclohexanol (TTC) as a highly effective chiral controller for the formation of the 2,5-substituted THF diol product with high diastereoselectivity (dr â¼973). Chiral resolution of (±)-TTC, prepared in one step from cyclohexene oxide, afforded (-)-(1S,2R)-TTC (er >991), which was applied to the synthesis of (+)-trans-(2S,5S)-linalool oxide.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Óxidos
/
Compostos de Tritil
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Compostos de Manganês
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Cicloexanóis
/
Monoterpenos
Idioma:
En
Ano de publicação:
2014
Tipo de documento:
Article