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2005
Alcohols
P 0110
09- 049
Diastereoselective Addition of Organozinc Reagents to 2-Alkyl-3-(arylsulfanyl)propanals. — It is found that steric and electronic effects of educts, amount and
nature of Lewis acid as well as the solvent used play an important role on the diastereoselective outcome of the title reaction. Best results are obtained employing ZnMe2 as
reagent, 1-1.2 equivalents of TiCl4 as Lewis acid, and CH2Cl2 as solvent. The products
are useful synthons: for example, the alcohols (IIIc) and (Xg) can smoothly be converted into the potential pine sawfly pheromone components (VIII) and (XI). —
(LARSSON, M.; GALANDRIN, E.; HOEGBERG*, H.-E.; Tetrahedron 60 (2004) 47,
10659-10669; Dep. Nat. Environ. Sci., Mid Swed. Univ.,
S-851 70 Sundsvall, Swed.; Eng.) — Jannicke
2005
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