Manganese-Catalyzed Stereospecific Hydroxymethylation of Alkyl Tosylates.
Journal
Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393
Informations de publication
Date de publication:
15 11 2019
15 11 2019
Historique:
pubmed:
7
11
2019
medline:
7
11
2019
entrez:
6
11
2019
Statut:
ppublish
Résumé
The development of a stereospecific hydroxymethylation of alkyl tosylates using an inexpensive, first-row catalyst is described. The transformation proceeds under mild conditions with low pressure to deliver homologated alcohols as products. Chiral, nonracemic β-branched primary alcohols are obtained with high enantiospecificity from easily accessed secondary alkyl substrates. Simple modification of the reaction system also permits access to α-
Identifiants
pubmed: 31689117
doi: 10.1021/acs.orglett.9b03706
pmc: PMC7147876
mid: NIHMS1575608
doi:
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.
Langues
eng
Sous-ensembles de citation
IM
Pagination
9268-9271Subventions
Organisme : NIGMS NIH HHS
ID : R35 GM118055
Pays : United States
Organisme : NIGMS NIH HHS
ID : R35 GM131708
Pays : United States
Références
Angew Chem Int Ed Engl. 2018 May 14;57(20):5867-5870
pubmed: 29504659
Chem Rev. 2015 Sep 23;115(18):9981-10080
pubmed: 26284754
Org Lett. 2010 Apr 2;12(7):1548-51
pubmed: 20199034
J Am Chem Soc. 2012 Jan 18;134(2):875-7
pubmed: 22188491
Org Lett. 2015 Oct 2;17(19):4794-7
pubmed: 26381108
Org Lett. 2016 May 20;18(10):2363-6
pubmed: 27135854
Angew Chem Int Ed Engl. 2019 Jul 8;58(28):9533-9536
pubmed: 31087438
J Am Chem Soc. 2017 Sep 13;139(36):12438-12440
pubmed: 28829914
Chem Commun (Camb). 2011 Oct 7;47(37):10254-6
pubmed: 21858308