Synthesis of Optically Sugar Alcohols by Diastereoselective Addition of Organozinc Reagents

Synthesis of Optically Sugar Alcohols by Diastereoselective Addition of Organozinc Reagents

Sachini, Maraisa; Lüdtke, Diogo S.

Abstract:

Enantioselective addition of organometallic reagents to aldehydes affords optically active secondary alcohols, components of many naturally occurring and biologically active compounds. Moreover they are also important as synthetic intermediates of various functionalities. Mixed organozinc reagents have played an important role, especially because of its low reactivity, which makes them suitable for the use in asymmetric catalysis. Considering our interest on the use of carbohydrates of as starting material for the synthesis of chiral molecules, and the peculiar reactivity pattern of organozinc reagents, particularly of type Zn-alkynyl-Alkyl and Zn-Aryl-Alkyl, in this report we present: The preparation of optically active secondary alcohols from diastereoselective addition of organozinc reagents to aldehydes obtained from sugars (D-mannitol, D-ribose and D-glucose).

Enantioselective addition of organometallic reagents to aldehydes affords optically active secondary alcohols, components of many naturally occurring and biologically active compounds. Moreover they are also important as synthetic intermediates of various functionalities. Mixed organozinc reagents have played an important role, especially because of its low reactivity, which makes them suitable for the use in asymmetric catalysis. Considering our interest on the use of carbohydrates of as starting material for the synthesis of chiral molecules, and the peculiar reactivity pattern of organozinc reagents, particularly of type Zn-alkynyl-Alkyl and Zn-Aryl-Alkyl, in this report we present: The preparation of optically active secondary alcohols from diastereoselective addition of organozinc reagents to aldehydes obtained from sugars (D-mannitol, D-ribose and D-glucose).

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_201391520343

Referências bibliográficas

• [1] 1 (a) Soai, K.; Nlwa, S. Chem. Rev. 1992, 92, 883. (b) Pu, L. and Yu, H. Chem. Rev. 2001, 101, 757.
• [2] 2 Wouters, A. D.; Bessa, Aa. B.; Sachini, M.; Wessjohann, L. A.; Ludtke, D. S. Synthesis 2013, 45, 2222.
• [3] 3 Raju, O. V. S.; Reddy, Y. V. R. Der Pharm.Chem. 2011, 3(5), 39.

Como citar:

Sachini, Maraisa; Lüdtke, Diogo S.; "Synthesis of Optically Sugar Alcohols by Diastereoselective Addition of Organozinc Reagents", p-95-95. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_201391520343