Carbohydrates - Tools for Stereoselective Synthesis by Mike Martin Kwabena Boysen

By Mike Martin Kwabena Boysen

Last a spot within the literature, this complete e-book provides such carbohydrate instruments as chiral auxiliaries, reagents, complicated ligands and organocatalysts, including information in their training, in addition to their winning program in stereoselective synthesis. It covers the synthesis of carbohydrate instruments, and discusses examples for a large variety of alternative reactions in comparison to these received with the easiest traditional methods.
An necessary resource for each natural chemist.

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Synth. , 350, 2339. Y. (2009) Chem. Eur. , 15, 9290. N. S. S. S. N. and Durst, T. (1999) J. Org. , 64, 7700. S. , 46, 4115. S. (2006) Tetrahedron, 62, 6303. 1 Introduction In this chapter we describe the 1,4-additions of various nucleophiles to α,βunsaturated carbonyl groups on carbohydrate templates. Many examples have revealed that carbohydrates serve as effective chiral auxiliaries for realizing useful levels of diastereoselectivity [1–8]. As acyclic 1,4-addition acceptors, acrylic amides or acrylic esters on a carbohydrate template are described.

For example, the 4-O-crotonyl ester 46 provided the 1,4-adducts 47 (R1 = i-propyl, ethyl, or t-butyl) most effectively when Et2AlCl was used as the Lewis acid. ) HO 2) 80% aq. ) Me = i-Pr, 90% de R1 = Et, 72% de R1 = t-Bu, 90% de 1) 4M KOH-MeOH, reflux, then 1M HCl 2) aniline, EDCI•HCl, DMAP, CH2Cl2 R1 O Me 48 (quant. for 2 steps) Synthesis of the 2,3-O-mesitoyl-type auxiliary 45 and the 1,4-additions of some alkyl radicals to its 4-O-crotonyl esters 46. 9 adducts 46, followed by treatment of the resulting β-alkylated butanoic acids 47 with aniline in the presence of N-(3-dimethylamino)propyl-N′-ethylcarbodiimide (EDCI).

1990) J. Am. Chem. , and Puff, H. , and Linden, A. (2002) J. Am. Chem. , 124, 8637 and references therein. (a) Córdova, A. (2004) Acc. Chem. P. L. (2002) Org. , 4, 3647. Kunz, H. and Schanzenbach, D. (1989) Angew. Chem. Int. Ed. , 28, 1068. , and El-Alali, A. R. (1991) J. Org. , 56, 1681. , and Schanzenbach, D. (1997) Angew. Chem. Int. Ed. , 36, 386. Allef, P. and Kunz, H. (2000) Tetrahedron: Asymmetry, 11, 375. Kunz, H. and Pfrengle, W. (1989) Angew. Chem. Int. Ed. , 28, 1067. , and Kunz, H. (1997) Synthesis, 1151.

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