Stereoselective Synthesis of 8-Trialkylstannylmenthols

Trialkyltin menthones of type 2 are obtained selectively by 1,4-addition of trialkylstannyl lithium to (-)-pulegone. Reduction of 2 with borane in THF using as catalyst the reagent prepared from borane and (S)-valinol gave a mixture of the corresponding trialkyltin alcohols 3 (Me: 84%; n-Bu: 90,6%)...

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Main Authors: Julio C. Podestá, Verónica Dodero, Nelda N. Giagante, Sandra D. Mandolesi
Format: Article
Language:English
Published: MDPI AG 2000-03-01
Series:Molecules
Subjects:
n/a
Online Access:http://www.mdpi.com/1420-3049/5/3/594/
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author Julio C. Podestá
Verónica Dodero
Nelda N. Giagante
Sandra D. Mandolesi
author_facet Julio C. Podestá
Verónica Dodero
Nelda N. Giagante
Sandra D. Mandolesi
author_sort Julio C. Podestá
collection DOAJ
description Trialkyltin menthones of type 2 are obtained selectively by 1,4-addition of trialkylstannyl lithium to (-)-pulegone. Reduction of 2 with borane in THF using as catalyst the reagent prepared from borane and (S)-valinol gave a mixture of the corresponding trialkyltin alcohols 3 (Me: 84%; n-Bu: 90,6%) and 4 (Me: 16% and n-Bu: 9,4%).
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spelling doaj.art-2445202e7891425491b8b2d64395445d2022-12-21T16:53:54ZengMDPI AGMolecules1420-30492000-03-015359459510.3390/50300594Stereoselective Synthesis of 8-TrialkylstannylmentholsJulio C. PodestáVerónica DoderoNelda N. GiaganteSandra D. MandolesiTrialkyltin menthones of type 2 are obtained selectively by 1,4-addition of trialkylstannyl lithium to (-)-pulegone. Reduction of 2 with borane in THF using as catalyst the reagent prepared from borane and (S)-valinol gave a mixture of the corresponding trialkyltin alcohols 3 (Me: 84%; n-Bu: 90,6%) and 4 (Me: 16% and n-Bu: 9,4%).http://www.mdpi.com/1420-3049/5/3/594/n/a
spellingShingle Julio C. Podestá
Verónica Dodero
Nelda N. Giagante
Sandra D. Mandolesi
Stereoselective Synthesis of 8-Trialkylstannylmenthols
Molecules
n/a
title Stereoselective Synthesis of 8-Trialkylstannylmenthols
title_full Stereoselective Synthesis of 8-Trialkylstannylmenthols
title_fullStr Stereoselective Synthesis of 8-Trialkylstannylmenthols
title_full_unstemmed Stereoselective Synthesis of 8-Trialkylstannylmenthols
title_short Stereoselective Synthesis of 8-Trialkylstannylmenthols
title_sort stereoselective synthesis of 8 trialkylstannylmenthols
topic n/a
url http://www.mdpi.com/1420-3049/5/3/594/
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