Facile and Highly Diastereoselective Synthesis of syn- and cis-1,2-Diol Derivatives from Protected alpha-Hydroxy Ketones

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F15%3A00454233" target="_blank" >RIV/61388963:_____/15:00454233 - 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>

Result language

angličtina

Original language name

Facile and Highly Diastereoselective Synthesis of syn- and cis-1,2-Diol Derivatives from Protected alpha-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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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

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Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2015

Confidentiality

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

Name of the periodical

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

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Volume of the periodical

2015

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

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