Ready access to enantiopure 5-substituted-3-pyrrolin-2-ones from N-benzyl-2,3-O-isopropylidene-d-glyceraldehyde nitrone (BIGN)

作者: Pedro Merino , Elena Castillo , Santiago Franco , Francisco L Merchan , Tomas Tejero

DOI: 10.1016/S0957-4166(98)00150-5

关键词:

摘要: Abstract The reaction of the lithiated salt methyl propiolate with N -benzyl-2,3- O -isopropylidene- d -glyceraldehyde nitrone (BIGN) afforded corresponding propargyl hydroxylamines in a stereocontrolled way depending on nature Lewis acid used as an additive. Subsequent reduction obtained provided chiral 5-substituted-3-pyrrolin-2-ones, high overall yields.

参考文章(49)
Wilfred Louis Florio Armarego, Douglas Dalzell Perrin, D. R Perrin, Purification of laboratory chemicals ,(1966)
Claus Herdeis, Andrea Aschenbrenner, Armin Kirfel, Franz Schwabenländer, Synthesis of and from S-pyroglutamic acid. Regio- and diastereoselective ring opening of its derivatives Tetrahedron-asymmetry. ,vol. 8, pp. 2421- 2432 ,(1997) , 10.1016/S0957-4166(97)00261-9
Pedro Merino, Ana Lanaspa, Francisco L. Merchan, Tomas Tejero, Stereoselective grignard reactions to α-amino nitrones. Synthesis of optically active α-aminohydroxylamines and 1,2-diamines Tetrahedron-asymmetry. ,vol. 8, pp. 2381- 2401 ,(1997) , 10.1016/S0957-4166(97)00250-4
Pedro Merino, Natalia Garces, Francisco L. Merchan, Tomas Tejero, Modified nucleosides from nitrones: a new and efficient stereoselective approach to isoxazolidinyl thymidine derivatives Chemical Communications. pp. 493- 494 ,(1998) , 10.1039/A705673G
Gloria Rassu, Luigi Pinna, Pietro Spanu, Fausta Ulgheri, Mara Cornia, Franca Zanardi, Giovanni Casiraghi, Asymmetric synthesis of 4-amino-2,3,4-trideoxyaldonic acids: novel gaba c-glycoconjugates Tetrahedron. ,vol. 49, pp. 6489- 6496 ,(1993) , 10.1016/S0040-4020(01)80163-0
Claudio Mazzini, Letitia Sambri, Henk Regeling, Binne Zwanenburg, Gordon J. F. Chittenden, Enantiospecific syntheses of (R)- and (S)-proline and some derivatives from D-glucono-1,5-lactone Journal of The Chemical Society-perkin Transactions 1. pp. 3351- 3356 ,(1997) , 10.1039/A704915C
S.H. Goh, Chen Wei, Abdul Razak Mohd. Ali, Strychnos - Aspidosperma alkaloids and a novel hydroxydilactam artefact from (Apocynaceae) Tetrahedron Letters. ,vol. 25, pp. 3483- 3484 ,(1984) , 10.1016/S0040-4039(01)91054-8
Anthony G. M. Barrett, Howard B. Broughton, A direct conversion of unprotected D-ribose into showdomycin and epishowdomycin The Journal of Organic Chemistry. ,vol. 49, pp. 3673- 3674 ,(1984) , 10.1021/JO00193A053
Nobuo Ikota, Stereocontrolled synthesis of 1,7a-diepialexine Tetrahedron Letters. ,vol. 33, pp. 2553- 2556 ,(1992) , 10.1016/S0040-4039(00)92240-8
C. Herdeis, H.P. Hubmann, Synthesis of homochiral R-baclofen from S-glutamic acid Tetrahedron-asymmetry. ,vol. 3, pp. 1213- 1221 ,(1992) , 10.1016/S0957-4166(00)82107-2