Stereocontrolled synthesis of highly functionalized quaternary carbon centers: a route to alpha-substituted serines.
Three in a row! Highly functionalized quaternary amino polyols with three consecutive asymmetric carbon centers have been prepared through tandem hydroboration of allene 1 and addition to an aldehyde (see scheme; Cy = cyclohexyl, TBDPS = tert-butyldiphenylsilyl, Ts = 4-toluenesulfonyl). This one-pot process provides access to advanced intermediates for the enantioselective synthesis of alpha-substituted serines.
Departamento de Química Orgànica, Fac. de Química, Institut de Biomedicina de la UB, Universitat de Barcelona, C/Martí i Franquès 1-11, 08028-Barcelona, Spain. xariza@ub.edu
Xavier
X
Ariza
Josep
J
Cornellà
Mercè
M
Font-Bardia
Jordi
J
Garcia
Jordi
J
Ortiz
Carolina
C
Sánchez
Xavier
X
Solans
D000466:Alkadienes / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000466:Alkadienes; D012694:Serine; C025947:propadiene; D002244:Carbon