66050-76-8Relevant articles and documents
Highly stereoselective allylic ethylation with alkoxytitanacyclopropane reagents. Synthesis of (1R/S,7R)-1,7-dimethylnonyl propanoate, the Western corn rootworm sex attractant
Isakov, Vladimir E.,Kulinkovich, Oleg G.
scheme or table, p. 6959 - 6961 (2009/04/07)
Allylic ethylation of 2-((E)-dodec-2-en-4-yloxy)tetrahydro-2H-pyran with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide proceeds via a SN2′ pathway to afford (E)-3-methyltridec-4-ene with excellent syn-diastereoselecivity. This transformation is used as a key step in the synthesis of (1R/S,7R)-1,7-dimethylnonyl propanoate, the Western corn rootworm (Diabrotica virgifera virgifera) sex attractant.
Application of modified Mosher's method for primary alcohols with a methyl group at C2 position.
Tsuda, Masashi,Toriyabe, Yuki,Endo, Tetsuya,Kobayashi, Jun'ichi
, p. 448 - 451 (2007/10/03)
The absolute configurations of a series of primary alcohols possessing a branched methyl group at C2 position were examined on the basis of a modified Mosher's method proposed by Minale et al. It was revealed that in many cases the absolute configurations
Assignment of the absolute configuration of β-chiral primary alcohols by NMR: Scope and limitations
Latypov, Shamil K.,Ferreiro, María J.,Qui?oá, Emilio,Riguera, Ricardo
, p. 4741 - 4751 (2007/10/03)
The prediction of the absolute configuration of β-chiral primary alcohols from the 1H NMR spectra of their esters with (R)- and (S)- 9-anthrylmethoxyacetic acids (9-AMA, 3) is discussed. Low-temperature NM experiments, MM, semiempirical, ab initio, and aromatic shielding effect calculations allowed the identification of the main conformers and showed that, in all alcohols for which the calculated ΔE(ag) (CVff) is in the range of 0.7-1.5 kcal/mol, conformer a/a is the most stable. A simple model for the assignment of the absolute configuration from NMR data is presented and its reliability corroborated with alcohols (8-20) of known configuration. Nevertheless, cyclic alcohols 21-23 have much higher ΔE(ag) values (2.2-3.1 kcal/mol) due to their different conformational composition, and their absolute configuration cannot be reliably predicted by this method.