Stereoselective polymer-supported synthesis of morpholine and thiomorpholine-3-carboxylic acid derivatives

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F17%3A73583711" target="_blank" >RIV/61989592:15110/17:73583711 - isvavai.cz</a>

Alternative codes found

RIV/61989592:15310/17:73583711

Result on the web

<a href="http://pubs.acs.org/doi/10.1021/acscombsci.6b00178" target="_blank" >http://pubs.acs.org/doi/10.1021/acscombsci.6b00178</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acscombsci.6b00178" target="_blank" >10.1021/acscombsci.6b00178</a>

Result language

angličtina

Original language name

Stereoselective polymer-supported synthesis of morpholine and thiomorpholine-3-carboxylic acid derivatives

Original language description

Herein we report the polymer-supported synthesis of 3,4-dihydro-2H-1,4-oxazine-3-carboxylic acid derivatives using immobilized Fmoc-Ser(tBu)-OH and Fmoc-Thr(tBu)-OH as the starting materials. After the solid-phase-synthesis of N-alkylated-N-sulfonylated/acylated intermediates, the target dihydro-oxazines were obtained using trifluoroacetic acid (TFA) mediated cleavage from the resin. This approach was also studied to the preparation of dihydro-thiazines from immobilized Fmoc-Cys(Trt)-OH. Inclusion of triethylsilane (TES) in the cleavage cocktail resulted in the stereoselective formation of the corresponding morpholine/thiomorpholine-3-carboxylic acids. Stereochemical studies revealed the specific configuration of the newly formed stereocenter and also the formation of stable N-acylmorpholine rotamers.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2017

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

ACS Combinatorial Science

ISSN

2156-8952

e-ISSN

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Volume of the periodical

19

Issue of the periodical within the volume

3

Country of publishing house

US - UNITED STATES

Number of pages

8

Pages from-to

173-180

UT code for WoS article

000396379900006

EID of the result in the Scopus database

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