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Stereocontrolled synthesis and cyclization of (+,−)-α,α’-dihydroxy-α,α ’, β-trimethylglutaric acid derivatives

Igor Viktorovich Vystorop 1
Igor Viktorovich Vystorop
, 
Ivan Ivanovich Chervin 2
Ivan Ivanovich Chervin
, 
Andrei Nikolaevich Utienyshev 1
Andrei Nikolaevich Utienyshev
, 
Carlos Jaime 3
Carlos Jaime
, 
Xavier Sanchez-Ruiz 3
Xavier Sanchez-Ruiz
,  , 
Remir Grigorevich Kostyanovsky 2
Remir Grigorevich Kostyanovsky
10.1070/MC1997v007n02ABEH000706
Published 1997-04-30
Communication , Volume 7, Issue 2, 64-66
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Vystorop I. V. et al. Stereocontrolled synthesis and cyclization of (+,−)-α,α’-dihydroxy-α,α ’, β-trimethylglutaric acid derivatives // Mendeleev Communications. 1997. Vol. 7. No. 2. pp. 64-66.
GOST all authors (up to 50) Copy
Vystorop I. V., Chervin I. I., Utienyshev A. N., Jaime C., Sanchez-Ruiz X., Aldoshin S. M., Kostyanovsky R. G. Stereocontrolled synthesis and cyclization of (+,−)-α,α’-dihydroxy-α,α ’, β-trimethylglutaric acid derivatives // Mendeleev Communications. 1997. Vol. 7. No. 2. pp. 64-66.
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TY - JOUR
DO - 10.1070/MC1997v007n02ABEH000706
UR - https://mendcomm.colab.ws/publications/10.1070/MC1997v007n02ABEH000706
TI - Stereocontrolled synthesis and cyclization of (+,−)-α,α’-dihydroxy-α,α ’, β-trimethylglutaric acid derivatives
T2 - Mendeleev Communications
AU - Vystorop, Igor Viktorovich
AU - Chervin, Ivan Ivanovich
AU - Utienyshev, Andrei Nikolaevich
AU - Jaime, Carlos
AU - Sanchez-Ruiz, Xavier
AU - Aldoshin, Sergei Mikhailovich
AU - Kostyanovsky, Remir Grigorevich
PY - 1997
DA - 1997/04/30
PB - Mendeleev Communications
SP - 64-66
IS - 2
VL - 7
ER -
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@article{1997_Vystorop,
author = {Igor Viktorovich Vystorop and Ivan Ivanovich Chervin and Andrei Nikolaevich Utienyshev and Carlos Jaime and Xavier Sanchez-Ruiz and Sergei Mikhailovich Aldoshin and Remir Grigorevich Kostyanovsky},
title = {Stereocontrolled synthesis and cyclization of (+,−)-α,α’-dihydroxy-α,α ’, β-trimethylglutaric acid derivatives},
journal = {Mendeleev Communications},
year = {1997},
volume = {7},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1997v007n02ABEH000706},
number = {2},
pages = {64--66},
doi = {10.1070/MC1997v007n02ABEH000706}
}
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Vystorop, Igor Viktorovich, et al. “Stereocontrolled synthesis and cyclization of (+,−)-α,α’-dihydroxy-α,α ’, β-trimethylglutaric acid derivatives.” Mendeleev Communications, vol. 7, no. 2, Apr. 1997, pp. 64-66. https://mendcomm.colab.ws/publications/10.1070/MC1997v007n02ABEH000706.

Abstract

Hydrocyanation of 3-methylpentane-2,4-dione stereospecifically gave trans,trans-iminolactone 1, whose configuration was established by X-ray diffraction of the corresponding lactone 2; the rate of cyclization of the diastereoisomeric lactonic acids 3a,b and their esters 4a,b into dilactone 5 was controlled sterically by the methyl groups with cis,cis-isomers 3b, 4b predominating ; alcoholysis of 5 regiospecifically afforded ester 4b.

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