446246-15-7Relevant articles and documents
Lithiated camphor-derived oxazolidinone S,N-acetals as chiral formyl anion synthons in additions to aldehydes. Asymmetric synthesis of α-hydroxy aldehydes and α-hydroxy acids
Gawley, Robert E.,Campagna, Silvio A.,Santiago, Marcelina,Ren, Tong
, p. 29 - 36 (2002)
N-(Phenylthiomethyl)oxazolidinones derived from camphor can be lithiated and added to aldehydes in good yields and stereoselectivities. The adducts are crystalline, which simplifies isolation of the major diastereomer from the product mixture. Hydrolysis affords enantiopure α-hydroxy aldehydes, which can be oxidized to α-hydroxy acids in good yields. The steric course of the reaction is analyzed in detail and a mechanistic model is presented.