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Issue 1, 2019
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Base mediated green synthesis of enantiopure 2-C-spiro-glycosyl-3-nitrochromenes

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Abstract

A novel green synthetic methodology has been developed to obtain enantiopure (2S)-2-C-spiro-glycosyl-3-nitrochromenes following the oxa-Michael–aldol condensation reaction of sugar derived 3-C-vinyl nitro olefins with substituted salicylaldehydes using Et3N as a base under neat conditions at rt–40 °C. The stereochemistry of the product is confirmed by a single crystal X-ray study. Several advantages are associated with this protocol such as cost effectiveness, easy accessibility, short reaction time, high yields, wide substrate scope and high enantiopurity.

Graphical abstract: Base mediated green synthesis of enantiopure 2-C-spiro-glycosyl-3-nitrochromenes

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Publication details

The article was received on 14 Sep 2018, accepted on 19 Nov 2018 and first published on 19 Nov 2018


Article type: Paper
DOI: 10.1039/C8OB02278J
Citation: Org. Biomol. Chem., 2019,17, 74-82

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    Base mediated green synthesis of enantiopure 2-C-spiro-glycosyl-3-nitrochromenes

    S. Nayak, P. Panda, B. P. Raiguru, S. Mohapatra and C. S. Purohit, Org. Biomol. Chem., 2019, 17, 74
    DOI: 10.1039/C8OB02278J

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