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  • Synthesis of Chiral 1,2-Oxazinanes and Isoxazolidines via Nitroso Aldol Reaction of Distal Dialdehydes.

Synthesis of Chiral 1,2-Oxazinanes and Isoxazolidines via Nitroso Aldol Reaction of Distal Dialdehydes.

Organic letters (2018-02-02)
Isai Ramakrishna, Panduga Ramaraju, Mahiuddin Baidya
摘要

The first catalytic enantioselective nitroso aldol reaction of distal dialdehydes is reported. The reaction is catalyzed by simple l-proline at room temperature and subsequent reduction delivered biologically potent and synthetically versatile N-O bond containing five- and six-membered heterocycles, 1,2-oxazinanes, and isoxazolidines in high yields and excellent enantioselectivities (up to >99% ee). The method was further exploited to prepare chiral 3-hydroxypiperidines and -pyrrolidines that are otherwise difficult to access.

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Sigma-Aldrich
3,5-二叔丁基儿茶酚, 98%