Abstract
Carbohydrates are abundant renewable resources and are a feedstock for green chemistry and sustainable synthesis of the future. Among the hexoses and the pentoses present in biomass, mannitol was selected in the present project as a valuable platform, directly available from the chiral pool, to build highly functionalized molecules. Starting from (R)-2,3-O-cyclohexylidene glyceraldehyde, which is easily prepared in a large scale from D-mannitol, an enantiopure chiral nitro alkene was prepared by reaction with nitromethane, and its reactivity studied. Organocatalytic Michael addition of dimethyl malonate, β-keto esters, and other nucleophiles on the nitro alkene afforded high stereoselectivity and densely functionalized chiral molecules, which were further synthetically developed, leading to five-membered lactones and bicyclic lactams. Preliminary studies showed that the metal-free catalytic reaction on the chiral nitro alkene can be performed under continuous flow conditions, thus enabling the use of (micro)mesofluidic systems for the preparation of enantiomerically pure organic molecules from the chiral pool.
Highlights
Efficient use of resources is the key to realizing sustainable growth through the development of new technologies with low environmental impact [1]
This article reports the catalytic Michael addition of dimethyl malonate and methyl phenylacetylacetate to the known sugar nitro reports olefin 2, which was obtained from addition (R)-2,3-O-cyclohexylidene glyceraldehyde
We started our with investigation on the reactivity of nitro
Summary
Efficient use of resources is the key to realizing sustainable growth through the development of new technologies with low environmental impact [1]. This will lead to the creation of new jobs [2]. New chemistry has to be developed in order to convert natural starting materials into a variety of chemicals comparable to the oil-derived ones. Such an effort asks for fundamental research covering a novel series of synthetic transformations from bio-based building blocks. An innovative series of fine chemicals, endowed with similar or improved properties (e.g., better biodegradability), will emerge from these studies [4]
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