Remarkable switch of regioselectivity in epoxide ring opening of 3-benzyl-7-oxa-3-azabicyclo[4.1.0]heptane with amines: practical synthesis of trans-4-amino-3-hydroxypiperidines and trans-3-amino-4-hydroxypiperidines

Autor:	Isao Kurimoto, Tetsuya Ikemoto, Osamu Tokuda, Toshiaki Aikawa
Rok vydání:	2010
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Heptane chemistry Organic Chemistry Drug Discovery Epoxide Organic chemistry Regioselectivity Ring (chemistry) Biochemistry Alkyl
Zdroj:	Tetrahedron Letters. 51:2832-2834
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2010.03.061
Popis:	A simple and highly C3 selective ring-opening method for 3,4-epoxypiperidines has been developed. We also describe a practical improvement of the C4 selective ring-opening method using the same N -alkyl substituted 3,4-epoxypiperidines. This method provides access to pharmaceutically relevant trans -3-amino-4-hydroxypiperidines and trans -4-amino-3-hydroxypiperidines with simple procedures.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0dc2e307cfcc5facdd0af8b85100eeff https://doi.org/10.1016/j.tetlet.2010.03.061 Zobrazit plný text záznamu Full Text from ScienceDirect