Enantioselective Allylations of Selected alpha, beta, gamma, delta-Unsaturated Aldehydes by Axially Chiral N,N'-dioxides. Synthesis of the Left-hand Part of Papulacandin D
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F16%3A10371963" target="_blank" >RIV/00216208:11310/16:10371963 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/16:00471657
Result on the web
<a href="http://dx.doi.org/10.2174/2213337203666160304193640" target="_blank" >http://dx.doi.org/10.2174/2213337203666160304193640</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.2174/2213337203666160304193640" target="_blank" >10.2174/2213337203666160304193640</a>
Alternative languages
Result language
angličtina
Original language name
Enantioselective Allylations of Selected alpha, beta, gamma, delta-Unsaturated Aldehydes by Axially Chiral N,N'-dioxides. Synthesis of the Left-hand Part of Papulacandin D
Original language description
Background: Catalytic asymmetric allylation of aldehydes is a synthetically useful method for preparation of chiral homoallylic alcohols that may serve as convenient synthetic building blocks. The catalysis can be brought about with Lewis acid or Lewis bases, and Bronsted acids. Objective: The main aim was to evaluate enantioselective allylation of variously substituted alpha, beta, gamma, delta-aldehydes with allyltrichlorosilane catalyzed by axially chiral Lewis bases with bis(tetrahybis(tetrahydroisoquinoline) N, N'-dioxide scaffold. Method: Allylations of several structurally different alpha, beta, gamma, delta-aldehydes were carried out in various solvents in the presence of a catalytic amount of an N, N'-dioxide to access conditions leading to the highest symmetric induction. Results: Out of screening of several reaction conditions the highest asymmetric induction (up to 98% ee) was achieved in THF. A higher asymmetric induction was observed with substrates bearing additional substituents on alpha-carbon atom. Allylation of (S)-(2E, 4E)-2,8-dimethyldecadienal gave rise to the corresponding homoallylic alcohol (an intermediate for synthesis of papulacandin D) with a high asymmetric induction of 92% ee. Conclusion: Enantioselective allylation of alpha, beta, gamma, delta-aldehydes with allyltrichlorosilane catalyzed by an axially chiral Lewis base gave rise to the corresponding homoallylic alcohols with a good enantioselection. This method could be used for synthesis of valuable building block for organic synthesis as it was demonstrated by a synthesis of a papulacandin D intermediate.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - 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
Result continuities
Project
<a href="/en/project/GAP207%2F11%2F0587" target="_blank" >GAP207/11/0587: Development and Application of Catalysts Based on Chiral Bipyridine Scaffold</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
CURRENT ORGANOCATALYSIS
ISSN
2213-3372
e-ISSN
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Volume of the periodical
3
Issue of the periodical within the volume
3
Country of publishing house
US - UNITED STATES
Number of pages
5
Pages from-to
301-305
UT code for WoS article
000406981800008
EID of the result in the Scopus database
2-s2.0-85047065832