Short syntheses of (S)-pipecolic acid, (R)-coniine, and (S)-δ-coniceine using biocatalytically-generated chiral building blocks

Autor:	Francisco Sánchez-Sancho, Bernardo Herradón
Rok vydání:	1998
Předmět:	Aspergillus species Chemistry Stereochemistry Organic Chemistry Catalysis Inorganic Chemistry chemistry.chemical_compound Coniine Yield (chemistry) Hydroxymethyl Piperidine Physical and Theoretical Chemistry Pipecolic acid
Zdroj:	Tetrahedron: Asymmetry. 9:1951-1965
ISSN:	0957-4166
DOI:	10.1016/s0957-4166(98)00178-5
Popis:	The kinetic resolutions of both (±)-N-(benzyloxycarbonyl-2-(hydroxymethyl)piperidine [(±)- 5 ] and (±)-N-( tert -butoxycarbonyl)-2-(hydroxymethyl)piperidine [(±)- 6 ] catalyzed by the enzyme acylase I from Aspergillus species (AA-I) afforded the chiral building blocks ( S )- 5 and ( S )- 6 , respectively; which were used for the syntheses of the title natural products and derivatives of ( S )-pipecolic acid. The syntheses were short (2–4 steps) and proceeded with satisfactory overall yield.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ec8faa4226174340a8afce9f18c1a5d3 https://doi.org/10.1016/s0957-4166(98)00178-5 Zobrazit plný text záznamu Full Text from ScienceDirect