Combination of Enabling Technologies to Improve and Describe the Stereoselectivity of Wolff–Staudinger Cascade Reaction

B. Musio; F. Mariani; E. P. Śliwiński; M. A. Kabeshov; H. Odajima; S. V. Ley

doi:10.1055/s-0035-1562579

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(20): 3515-3526
DOI: 10.1055/s-0035-1562579

paper

Combination of Enabling Technologies to Improve and Describe the Stereoselectivity of Wolff–Staudinger Cascade Reaction

B. Musio

^aUniversity of Cambridge, Department of Chemistry, Lensfield Road, Cambridge, CB2 1EW, UK eMail: svl1000@cam.ac.uk

,

F. Mariani

^aUniversity of Cambridge, Department of Chemistry, Lensfield Road, Cambridge, CB2 1EW, UK eMail: svl1000@cam.ac.uk

^bUniversitat de Barcelona, Laboratori de Química Orgànica, Facultat de Farmàcia, Av. Joan XXIII s/n, 08028 Barcelona, Spain

,

E. P. Śliwiński

^aUniversity of Cambridge, Department of Chemistry, Lensfield Road, Cambridge, CB2 1EW, UK eMail: svl1000@cam.ac.uk

,

M. A. Kabeshov

^aUniversity of Cambridge, Department of Chemistry, Lensfield Road, Cambridge, CB2 1EW, UK eMail: svl1000@cam.ac.uk

,

H. Odajima

^cSaida FDS, 143-10 Itsushiki, Yaizu-shi, Shizuoka Prefecture 4250054, Japan

,

S. V. Ley*

^aUniversity of Cambridge, Department of Chemistry, Lensfield Road, Cambridge, CB2 1EW, UK eMail: svl1000@cam.ac.uk

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Abstract

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Abstract

A new, single-mode bench-top resonator was evaluated for the microwave-assisted flow generation of primary ketenes by thermal decomposition of α-diazoketones at high temperature. A number of amides and β-lactams were obtained by ketene generation in situ and reaction with amines and imines, respectively, in good to excellent yields. The preferential formation of trans-configured β-lactams was observed during the [2+2] Staudinger cycloaddition of a range of ketenes with different imines under controlled reaction conditions. Some insights into the mechanism of this reaction at high temperature are reported, and a new web-based molecular viewer, which takes advantage from Augmented Reality (AR) technology, is also described for a faster interpretation of computed data.

Key words

microwave - Wolff - Staudinger - flow - Augmented Reality - molecular visualisation

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