Synthesis 2012; 44(22): 3421-3431
DOI: 10.1055/s-0032-1317483
short review
© Georg Thieme Verlag Stuttgart · New York

Catalyst-Controlled Regioselective Reactions of Carbohydrate Derivatives

Doris Lee
Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON, M5S 3H6, Canada   Fax: +1(416)9788775   Email: mtaylor@chem.utoronto.ca
,
Mark S. Taylor*
Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON, M5S 3H6, Canada   Fax: +1(416)9788775   Email: mtaylor@chem.utoronto.ca
› Author Affiliations
Further Information

Publication History

Received: 02 August 2012

Accepted after revision: 26 September 2012

Publication Date:
17 October 2012 (online)


Abstract

The efficient synthesis of oligosaccharides requires methods for regioselective manipulation of hydroxyl groups in monosaccharide derivatives. Catalysis represents a potentially general solution to this problem, and over the past decade, the development of catalyst-controlled methods for regioselective functionalization of carbohydrates has intensified. This Short Review highlights the range of catalysts and catalytic mechanisms that may be exploited to alter the reactivity of hydroxyl groups in carbohydrate substrates.

1 Introduction

2 Intrinsic Trends in the Reactivity of Carbohydrate Hydroxyl Groups

2.1 Steric Control

2.2 Electronic Control

3 Enzyme Catalysis

4 Phase-Transfer Catalysis

5 Lewis Base Catalysis

5.1 Peptide-Based Catalysts

5.2 Modified DMAP Catalysts

5.3 Chiral Amines

6 Lewis Acid Catalysis

6.1 Tin(IV) Reagents

6.2 Transition-Metal Reagents

6.3 Lanthanum(III) Reagents

6.4 Multistep One-Pot Methods

6.5 Organoboron Reagents

7 Conclusions and Outlook

 
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