Reversal of the sense of enantioselectivity between 1-and 2-aza[6]helicenes used as chiral inducers of asymmetric autocatalysis

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F17%3A00475000" target="_blank" >RIV/61388963:_____/17:00475000 - isvavai.cz</a>

Result on the web

<a href="http://pubs.rsc.org/en/content/articlehtml/2013/ob/c6ob02745h" target="_blank" >http://pubs.rsc.org/en/content/articlehtml/2013/ob/c6ob02745h</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/c6ob02745h" target="_blank" >10.1039/c6ob02745h</a>

Result language

angličtina

Original language name

Reversal of the sense of enantioselectivity between 1-and 2-aza[6]helicenes used as chiral inducers of asymmetric autocatalysis

Original language description

Reversal of the sense of enantioselectivity was observed between 1-aza[6]helicene 2 and 2-aza[6]helicene 3 employed as chiral inducers of asymmetric autocatalysis of pyrimidyl alkanol. In the presence of (P)-(+)-1-aza[6]helicene 2, the reaction of pyrimidine-5-carbaldehyde 1 with diisopropylzinc afforded, in conjunction with asymmetric autocatalysis, (S)-pyrimidyl alkanol 4 with high ee. Surprisingly, the reaction in the presence of (P)-(+)-2-aza[6]helicene 3 gave the opposite enantiomer of (R)-alkanol 4 with high ee. In the same manner, (M)-(-)-2 and (M)-(-)-3 afforded (R)-and (S)-alkanol 4, respectively. The sense of enantioselectivity is controlled not only by the helicity of the azahelicene derivatives but also by the position of the nitrogen atom.

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

<a href="/en/project/GA14-29667S" target="_blank" >GA14-29667S: The preparation of enantiopure helically chiral aromatics and their use in catalysis</a><br>

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

Organic & Biomolecular Chemistry

ISSN

1477-0520

e-ISSN

—

Volume of the periodical

15

Issue of the periodical within the volume

6

Country of publishing house

GB - UNITED KINGDOM

Number of pages

4

Pages from-to

1321-1324

UT code for WoS article

000395882500005

EID of the result in the Scopus database

2-s2.0-85011886733