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Efficient One-Pot Synthesis of Enantiomerically Pure 2-(Hydroxymethyl)morpholines

Title data

Breuning, Matthias ; Winnacker, Malte ; Steiner, Melanie:
Efficient One-Pot Synthesis of Enantiomerically Pure 2-(Hydroxymethyl)morpholines.
In: European Journal of Organic Chemistry. (2007) Issue 13 . - pp. 2100-2106.
ISSN 1099-0690
DOI: https://doi.org/10.1002/ejoc.200601006

Abstract in another language

An efficient and convenient one-pot procedure for the synthesis of enantiomerically pure 2-(hydroxymethyl)morpholines with a widely variable substitution pattern was developed. Addition of chiral β-amino alcohols to (S)- or (R)-epichlorohydrin in the presence of LiClO4 afforded the corresponding chloro alcohols, which were treated with NaOMe to give the epoxides and, by subsequent intramolecular cyclization, the target compounds in good yields (57–77 %).

Further data

Item Type: Article in a journal
Refereed: Yes
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry > Professor Organic Chemistry - Univ.-Prof. Dr. Matthias Breuning
Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry
Result of work at the UBT: No
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 11 Jan 2022 14:47
Last Modified: 11 Jan 2022 14:47
URI: https://eref.uni-bayreuth.de/id/eprint/68320