Facile and Highly Diastereoselective Synthesis of syn- and cis-1,2-Diol Derivatives from Protected -Hydroxy Ketones
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F15%3A10316608" target="_blank" >RIV/00216208:11310/15:10316608 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201501174" target="_blank" >http://dx.doi.org/10.1002/ejoc.201501174</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201501174" target="_blank" >10.1002/ejoc.201501174</a>
Alternative languages
Result language
angličtina
Original language name
Facile and Highly Diastereoselective Synthesis of syn- and cis-1,2-Diol Derivatives from Protected -Hydroxy Ketones
Original language description
An efficient method for the synthesis of monoprotected syn- or cis-1,2-diol derivatives by reduction of easily accessible -(2,2,6,6-tetramethylpiperidinyloxy) ketones is reported. The -(tetramethylpiperidinyloxy) group as the stereodirecting group induces in unhindered acyclic or cyclic ketones complete syn- or cis-diastereoselectivity, respectively, with L-Selectride. For more hindered derivatives, where L-Selectride becomes unreactive, LiAlH4 proved effective, essentially showing the same high selectivity. The diastereoselectivity of the reduction can be rationalized for acyclic ketones by the Felkin-Anh model, whereas for cyclic substrates, attack from the face opposite to the tetramethylpiperidinyloxy group predictably prevails with high selectivity regardless of the substitution pattern. The liberation of free diols was achieved by reductive N-O bond cleavage of the alkoxyamine unit.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
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Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2015
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
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Volume of the periodical
neuveden
Issue of the periodical within the volume
35
Country of publishing house
DE - GERMANY
Number of pages
14
Pages from-to
7785-7798
UT code for WoS article
000366426600019
EID of the result in the Scopus database
2-s2.0-84948798902