87732-55-6Relevant articles and documents
Asymmetric Michael Additions. Regio-, Diastereo-, and Enantioselective Alkylations of the Enamines from β-Tetralones and (S)-2-(Methoxymethyl)pyrrolidine ("Prolinol Methyl Ether") by ω-Nitrostyrenes
Blarer, Stefan J.,Seebach, Dieter
, p. 3086 - 3096 (2007/10/02)
β-Tetralones with various substituents (CH3, NO2, OCH3, OCH2O, Cl) in 1-, 5-, 6-, 7-, and 8-position are added to ω-nitrostyrenes (2) through enamines (1) derived from (S)-2-(methoxymethyl)pyrrolidine.Hydrolysis of the primary adducts (3) yields (35 - 55percent) β-tetralones 4 alkylated in the 3-position.These are all > 90percent diastereomerically and 75 - 99percent optically pure (see u-4 and Table 1).From results of earlier investigations it is inferred, that the present reaction occurs with relative topicity lk, ul-1,4 (see 6), i.e. that the products 4 have (3S,1'R)-configuration.This is compatible with the 1H NMR and CD spectra of the isolated products of type 4.