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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.

Organic letters (2014-09-17)
Ali M Al Hazmi, Nadeem S Sheikh, Carole J R Bataille, Azzam A M Al-Hadedi, Sam V Watkin, Tim J Luker, Nicholas P Camp, Richard C D Brown
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 ∼97:3). Chiral resolution of (±)-TTC, prepared in one step from cyclohexene oxide, afforded (-)-(1S,2R)-TTC (er >99:1), which was applied to the synthesis of (+)-trans-(2S,5S)-linalool oxide.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Linalool, 97%
Supelco
Linalool, analytical standard
Sigma-Aldrich
Linalool, ≥97%, FCC, FG