TY - JOUR
T1 - Versatile synthesis of quaternary 1,3-oxazolidine-2,4-diones and their use in the preparation of α-hydroxyamides
AU - Merino, Omar
AU - Santoyo, Blanca M.
AU - Montiel, Luisa E.
AU - Jiménez-Vázquez, Hugo A.
AU - Zepeda, L. Gerardo
AU - Tamariz, Joaquín
N1 - Funding Information:
We are grateful to Daniel Zárate for the experimental assistance, to Drs. Eleuterio Burgueño, Francisco Delgado, and Francisco Díaz for spectrometric measurements, and Bruce Allan Larsen for reviewing the English in the manuscript. J.T. acknowledges SIP/IPN (Grants 20070339 , 20080527 , 20090519 , and 20100236 ) and CONACYT (Grants 43508-Q and 83446 ) for the financial support. O.M., B.M.S., and L.E.M. thank CONACYT for the scholarships awarded. L.G.Z. and J.T. are fellows of the EDI-IPN and COFAA-IPN programs.
PY - 2010/7/21
Y1 - 2010/7/21
N2 - A new approach to the synthesis of 1,3-oxazolidine-2,4-diones, via a two-step reaction sequence, starting from the readily available α-ketols and isocyanates, is reported. The condensation of the latter led to the key precursors 4-methylene-2-oxazolidinones, which are converted into the diones by an oxidative cleavage of the exocyclic double bond. Thus, 5,5-disubstituted 1,3-oxazolidine-2,4-diones can be accessed in good yields from the appropriate functionalized a-ketols. Moreover, two alternative routes are also described either by functionalization of 4-oxazolin-2-ones or by alkylation of the 1,3-oxazolidine-2,4-dione core previously prepared. Upon hydrolysis of the 1,3-oxazolidine-2,4-diones, a series of a-hydroxyamides bearing a quaternary stereocenter were obtained.
AB - A new approach to the synthesis of 1,3-oxazolidine-2,4-diones, via a two-step reaction sequence, starting from the readily available α-ketols and isocyanates, is reported. The condensation of the latter led to the key precursors 4-methylene-2-oxazolidinones, which are converted into the diones by an oxidative cleavage of the exocyclic double bond. Thus, 5,5-disubstituted 1,3-oxazolidine-2,4-diones can be accessed in good yields from the appropriate functionalized a-ketols. Moreover, two alternative routes are also described either by functionalization of 4-oxazolin-2-ones or by alkylation of the 1,3-oxazolidine-2,4-dione core previously prepared. Upon hydrolysis of the 1,3-oxazolidine-2,4-diones, a series of a-hydroxyamides bearing a quaternary stereocenter were obtained.
KW - 1,3-Oxazolidine-2,4-diones
KW - Oxidative cleavage
KW - Quaternary stereocenters
KW - m-Chloroperbenzoic acid
KW - α-Hydroxyamides
UR - http://www.scopus.com/inward/record.url?scp=77954312096&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2010.05.034
DO - 10.1016/j.tetlet.2010.05.034
M3 - Artículo
SN - 0040-4039
VL - 51
SP - 3738
EP - 3742
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 29
ER -