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

Autor:	Panduga Ramaraju, Isai Ramakrishna, Mahiuddin Baidya
Rok vydání:	2018
Předmět:	010405 organic chemistry Organic Chemistry Enantioselective synthesis Nitroso 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Aldol reaction Physical and Theoretical Chemistry
Zdroj:	Organic Letters. 20:1023-1026
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.7b03968
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::2c21ee38f451b0dc4c18cec40d0dbcaf https://doi.org/10.1021/acs.orglett.7b03968 Zobrazit plný text záznamu