Next Article in Journal
Antiproliferative Benzoindazolequinones as Potential Cyclooxygenase-2 Inhibitors
Previous Article in Journal
Synthesis and Properties of New Dithienosilole Derivatives as Luminescent Materials
Previous Article in Special Issue
Electrophilic Bromination in Flow: A Safe and Sustainable Alternative to the Use of Molecular Bromine in Batch
Open AccessFeature PaperArticle

Evaluation of In-Batch and In-Flow Synthetic Strategies towards the Stereoselective Synthesis of a Fluorinated Analogue of Retro-Thiorphan

1
Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy
2
Istituto di Scienze e Tecnologie Molecolari–ISTM-CNR, Via Golgi 19, 20133 Milano, Italy
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(12), 2260; https://doi.org/10.3390/molecules24122260
Received: 8 May 2019 / Revised: 10 June 2019 / Accepted: 12 June 2019 / Published: 18 June 2019
(This article belongs to the Special Issue Flow Chemistry in Organic Synthesis)
A stereoselective synthetic strategy for the preparation of trifluoromethylamine mimics of retro-thiorphan, involving a diastereoselective, metal-free catalytic step, has been studied in batch and afforded the target molecule in good yields and high diastereoselectivity. A crucial point of the synthetic sequence was the catalytic reduction of a fluorinated enamine with trichlorosilane as reducing agent in the presence of a chiral Lewis base. The absolute configuration of the key intermediate was unambiguously assigned by X-ray analysis. The synthesis was also investigated exploiting continuous flow reactions; that is, an advanced intermediate of the target molecule was synthesized in only two in-flow synthetic modules, avoiding isolation and purifications of intermediates, leading to the isolation of the target chiral fluorinated amine in up to an 87:13 diastereoisomeric ratio. View Full-Text
Keywords: fluorinated derivatives; flow chemistry; organocatalysis; stereoselective synthesis; reduction fluorinated derivatives; flow chemistry; organocatalysis; stereoselective synthesis; reduction
Show Figures

Graphical abstract

MDPI and ACS Style

Pirola, M.; Puglisi, A.; Raimondi, L.; Forni, A.; Benaglia, M. Evaluation of In-Batch and In-Flow Synthetic Strategies towards the Stereoselective Synthesis of a Fluorinated Analogue of Retro-Thiorphan. Molecules 2019, 24, 2260.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop