Georg Thieme Verlag KG
Synthesis
,  том 56 ,  издание 04 ,  страницы 577-584

Efficient and scalable synthesis of 6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one through organocatalyzed desymmetrization and chemoselective reduction

Pierre Georges Echeverria 1
, 
Guillaume Tintori 1
, 
Clément Jacob 1
, 
Christine Delsarte 1
, 
François Potié 1
, 
Laurence Grimaud 2
, 
Maxime Vitale 2
1
 
Minakem Recherche
2
 
LBM
Тип публикации: Journal Article
Дата публикации: 2023-11-23
Georg Thieme Verlag KG
scimago Q2
wos Q2
БС2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Краткое описание

The development of a robust process to 6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one, a key intermediate toward several active compounds of interest, is described. A scalable organocatalyzed desymmetrization was first studied and the reaction proved to be compatible with standard dilution. A kinetic study was performed to elucidate substrate and catalyst concentration dependences. Next, a chemoselective reduction of the carboxylic acid was developed. The scalability was demonstrated on 100 g scale through a fully telescoped process.

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Echeverria P. G. et al. Efficient and scalable synthesis of 6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one through organocatalyzed desymmetrization and chemoselective reduction // Synthesis. 2023. Vol. 56. No. 04. pp. 577-584.
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Echeverria P. G., Tintori G., Jacob C., Delsarte C., Potié F., Grimaud L., Vitale M. Efficient and scalable synthesis of 6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one through organocatalyzed desymmetrization and chemoselective reduction // Synthesis. 2023. Vol. 56. No. 04. pp. 577-584.
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TY - JOUR
DO - 10.1055/a-2217-0996
UR - https://doi.org/10.1055/a-2217-0996
TI - Efficient and scalable synthesis of 6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one through organocatalyzed desymmetrization and chemoselective reduction
T2 - Synthesis
AU - Echeverria, Pierre Georges
AU - Tintori, Guillaume
AU - Jacob, Clément
AU - Delsarte, Christine
AU - Potié, François
AU - Grimaud, Laurence
AU - Vitale, Maxime
PY - 2023
DA - 2023/11/23
PB - Georg Thieme Verlag KG
SP - 577-584
IS - 04
VL - 56
SN - 0039-7881
SN - 1437-210X
ER -
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@article{2023_Echeverria,
author = {Pierre Georges Echeverria and Guillaume Tintori and Clément Jacob and Christine Delsarte and François Potié and Laurence Grimaud and Maxime Vitale},
title = {Efficient and scalable synthesis of 6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one through organocatalyzed desymmetrization and chemoselective reduction},
journal = {Synthesis},
year = {2023},
volume = {56},
publisher = {Georg Thieme Verlag KG},
month = {nov},
url = {https://doi.org/10.1055/a-2217-0996},
number = {04},
pages = {577--584},
doi = {10.1055/a-2217-0996}
}
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Echeverria, Pierre Georges, et al. “Efficient and scalable synthesis of 6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one through organocatalyzed desymmetrization and chemoselective reduction.” Synthesis, vol. 56, no. 04, Nov. 2023, pp. 577-584. https://doi.org/10.1055/a-2217-0996.