180986-88-3Relevant academic research and scientific papers
(R)-2,3-O-cyclohexylideneglyceraldehyde, a versatile intermediate for asymmetric synthesis of homoallyl and homopropargyl alcohols in aqueous medium
Chattopadhyay, Angshuman
, p. 6104 - 6107 (1996)
Zn-mediated allylation and propargylation of (R)2,3-O-cyclohexylideneglyceraldehyde (1) in aqueous medium following Luche's procedure afforded the anti homoallylic 3 and homopropargylic 8 alcohols in good yield and with high stereoselectivity. Crotylation of 1 under similar conditions afforded appreciable amounts of erythro-5 and threo-6 alcohols. In each case, the diastereo alcohols are separable by column chromatography. Compound 8 on appropriate chemical manipulation of its functionalities gave the (S)-enantiomer of (R)-13, a useful synthon of LTB4. Compound 3 on chemical elaboration afforded a diversely functionalized triol derivative 15, a potentially useful synthon for many bioactive compounds.
