title: Asymmetric synthesis of succinic semialdehyde derivatives.
abstract: The nucleophilic Michael addition of 2-(diphenylmethoxymethyl)-1-methyleneamino pyrrolidine 1Dto prochiral aliphatic and aromatic alkylidene malonates 2 takes place in the presence of MgI(2) to afford the corresponding Michael adducts 3 in excellent yields and good selectivities. In the aromatic series, optically pure (de > 98%) major diastereomers (S,S)-3 were isolated in good yields (77-93%) after chromatographic separation. Direct, racemization-free BF(3).OEt(2)-catalyzed thiolysis of compounds 3 afforded dithioacetals 7. These compounds were transformed into malonates 8 and succinic semialdehyde derivatives 9 by Raney Nickel mediated desulfuration or decarboxylation, respectively.
authors.affiliation: Instituto de Investigaciones Químicas (CSIC-USe), Isla de la Cartuja, Americo Vespucio s/n, E-41092 Seville, Spain. jmlassa@cica.es
authors.forename: José M
authors.initials: JM
authors.lastname: Lassaletta
authors.forename: Juan
authors.initials: J
authors.lastname: Vázquez
authors.forename: Auxiliadora
authors.initials: A
authors.lastname: Prieto
authors.forename: Rosario
authors.initials: R
authors.lastname: Fernández
authors.forename: Gerhard
authors.initials: G
authors.lastname: Raabe
authors.forename: Dieter
authors.initials: D
authors.lastname: Enders