105017-31-0Relevant articles and documents
Activation of N-Sulfonyl oxaziridines using copper(II) catalysts: Aminohydroxylations of styrenes and 1,3-dienes
Michaelis, David J.,Ischay, Michael A.,Yoon, Tehshik P.
, p. 6610 - 6615 (2008)
N-Sulfonyl oxaziridines are susceptible to electrophilic activation using copper(II) catalysts and react with styrenes under these conditions to provide 1,3-oxazolidines in a formal aminohydroxylation of the alkene. We propose a two-step mechanism involving a cationic intermediate to account for the rate differences and regioselectivities observed using a variety of styrenes. In accord with our hypothesis, aminohydroxylations of a range of substrates bearing electron-stabilizing groups are successful, and 1,3-dienes are particularly good substrates for copper(II)-catalyzed aminohydroxylation. Reactions of unsymmetrical dienes provide good to excellent olefin selectivity, the sense and magnitude of which can be rationalized upon consideration of the stability of the cationic intermediates suggested by our mechanism. Diastereoselective synthesis of a diverse range of densely functionalized structures can be achieved by polyfunctionalization of dienes using aminohydroxylation as a key complexity-increasing step.
Efficient synthesis of 3-hydroxyprolines and 3-hydroxyprolinols from sugars
Lee, Jin Hwan,Kang, Jae Eun,Yang, Min Suk,Kang, Kyu Young,Park, Ki Hun
, p. 10071 - 10076 (2007/10/03)
trans-3-Hydroxy-L-proline 1, trans-3-hydroxy-L-prolinol 2, cis-3-hydroxy-D-proline 3, and cis-3-hydroxy-D-prolinol 4 have been prepared in enantiomerically pure form with chirospecific manner. Key intermediates, 2-amino-3-hydroxy-4-pentenoate 9 and 17, were obtained from D-glucono-δ-lactone and L-gulonic acid γ-lactone via a simultaneous dealkoxyhalogenation.
A flexible synthesis of azasugars and homoazasugars via olefin metathesis
Huwe, Christoph M.,Blechert, Siegfried
, p. 61 - 67 (2007/10/03)
A flexible synthesis of azasugars and homoazasugars from vinyl glycine methyl ester is described. The syntheses, which are based on ring closing olefin metathesis steps and stereocontrolled functionalizations of the formed double bonds, offer a broad vari