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Catalytic Activation of Carbohydrates as Formaldehyde Equivalents for Stetter Reaction with Enones

Junmin Zhang, Chong Xing, Bhoopendra Tiwari and Yonggui Robin Chi*

*Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore, Email: robinchintu.edu.sg

J. Zhang, C. Xing, B. Tiwari, Y. R. Chi, J. Am. Chem. Soc., 2013, 135, 8113-8116.

DOI: 10.1021/ja401511r (free Supporting Information)


Abstract

N-heterocyclic carbene (NHC)-catalyzed C-C bond cleavage of carbohydrates as formaldehyde equivalents generates acyl anion intermediates for Stetter reaction via a retro-benzoin-type process. The renewable nature of carbohydrates, accessible from biomass, further highlights the practical potential of this fundamentally interesting catalytic activation.

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Key Words

Stetter Reaction, Microwave Synthesis, Organocatalysis, Green Chemistry


ID: J48-Y2013