Synthesis 2016; 48(20): 3515-3526
DOI: 10.1055/s-0035-1562579
paper
© Georg Thieme Verlag Stuttgart · New York

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

B. Musio
a  University of Cambridge, Department of Chemistry, Lensfield Road, Cambridge, CB2 1EW, UK   Email: svl1000@cam.ac.uk
,
F. Mariani
a  University of Cambridge, Department of Chemistry, Lensfield Road, Cambridge, CB2 1EW, UK   Email: svl1000@cam.ac.uk
b  Universitat de Barcelona, Laboratori de Química Orgànica, Facultat de Farmàcia, Av. Joan XXIII s/n, 08028 Barcelona, Spain
,
E. P. Śliwiński
a  University of Cambridge, Department of Chemistry, Lensfield Road, Cambridge, CB2 1EW, UK   Email: svl1000@cam.ac.uk
,
M. A. Kabeshov
a  University of Cambridge, Department of Chemistry, Lensfield Road, Cambridge, CB2 1EW, UK   Email: svl1000@cam.ac.uk
,
H. Odajima
c  Saida FDS, 143-10 Itsushiki, Yaizu-shi, Shizuoka Prefecture 4250054, Japan
,
S. V. Ley*
a  University of Cambridge, Department of Chemistry, Lensfield Road, Cambridge, CB2 1EW, UK   Email: svl1000@cam.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 11 July 2016

Accepted after revision: 07 August 2016

Publication Date:
10 August 2016 (online)


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.

Supporting Information

 
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