Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 35, Pages 8918-8927Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202100321
Keywords
cycloadditions; sulfinylamines; sulfoximines; sulfonimidamides; sulfur
Categories
Funding
- EPSRC Centre for Doctoral Training in Synthesis for Biology and Medicine [EP/L015838/1]
- GlaxoSmithKline
- Vertex
- AstraZeneca
- Diamond Light Source
- Defence Science and Technology Laboratory
- Evotec
- Janssen
- Novartis
- Pfizer
- Syngenta
- Takeda
- UCB
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Sulfinylamines, known for their reactivity as sulfur electrophiles and in Diels-Alder reactions, have been underutilized in organic synthesis in recent decades. Recent research has shown their potential in one-pot syntheses of sulfoximines and sulfonimidamides, highlighting their different reactivity modes and unappreciated potential.
Sulfinylamines (R-N=S=O), monoaza analogues of sulfur dioxide, have been known for well over a century, and their reactivity as sulfur electrophiles and in Diels-Alder reactions is well-established. However, they have only rarely been used in organic synthesis in recent decades despite the increasing prominence of compounds containing N=S=O functionality, such as sulfoximines and sulfonimidamides. This Minireview aims to bring wider visibility to the unique chemistry enabled by this class of compounds. We focus on advances from the last 10 years, including the first examples of their use in the one-pot syntheses of sulfoximines and sulfonimidamides. Also covered are the reactions of sulfinylamines with carbon-centred radicals, their use for formation of heterocycles through cycloadditions, and catalytic enantioselective allylic oxidation of alkenes via a hetero-ene reaction. These examples highlight the different reactivity modes of sulfinylamines and their underappreciated potential for forming molecules which contain high- or low-valent sulfur, or even no sulfur at all.
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